ROAD MAP (3) PROBLEM

O H CH 2–Ph O H CH2–Ph O
O
N N NH2
N N N
N O O
H CH2–Ph H
H N–H N–H
O
Complete hydrolysis

(A) + (B) + (C) In which A and B

Borane Soda-lime / D are naturally
occuring amino-acid
(D) O (G) and amino acid "B"
(i) NaNO2 + HCl has one chiral center
Et – O – C – O – Et
(1 eq.) (ii) PCl5
(iii) L.A.H. In Baeyer Villiger
(E) oxidation we assume
O (H) following migrating
HNO3 / H
+ aptitude
Cl / Base
(1 eq.) NO 2
(F) (I) [O–substituted] –H> –Ph> >–Et>–Me
Number of
N.B.S.
chiral center in 'F'
(J)
H
. KO alc.KOH / D
aq
(K) HBr (Me)2CuLi (i) KMnO4 / OH–
O3 (Q) (R) (S) (T)
C r one Peroxide +
(ii) H
et H.B.O. NH3 / D
Ac
(L)
(W) (U)
mcpba
Fe + NH 4Cl NaOBr
(M)
(X) (V)
Fe + NH4Cl CrO3 + Acetone
60°C
(Y)
(N)
4 < PH < 6
PH = 9
(Z)
(O)
Br2 + H2O

(P)