Pyridine → Methyl N-[(benzyloxy)carbonyl]-L-valinate

HRID 1112331Notes

Reaction equation

HRID 1112331 reaction equation
[CH3:1][CH:2]([C@H:4]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:5]([OH:7])=[O:6])[CH3:3].N1C=CC=C[CH:20]=1.Cl.COC(=O)[C@H](C(C)C)N>C(Cl)(Cl)Cl>[NH:8]([C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C@H:4]([C:5]([O:7][CH3:20])=[O:6])[CH:2]([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 111190Methyl valinate hydrochlorideHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 10967417Methyl N-[(benzyloxy)carbonyl]-L-valinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.61 g of the resin 6a obtained according to Instruction (5b) are stirred in 40 ml of chloroform with 0.50 ml of pyridine and 0.350g of L-valine methyl ester hydrochloride for 130 minutes. The resin is filtered off and washed with 200 ml of chloroform and the filtrate is worked up as described in the previous Example. The yield is 0.300 g of Z-Val-Val-OMe and the melting point of the crude product is 120° C.; according to the IR and NMR spectrum, this product is identical to the authentic comparative preparation.

Workup

  1. filtrationThe resin is filtered off
  2. washwashed with 200 ml of chloroform
  3. customis 120° C.
  4. customthis product is identical to the authentic comparative preparation

Sources & evidence

ORD record
ord-c24a239c14ec49a1a43fe87e733aa2ad
Source dataset
uspto-grants-1978_10
Patent number
US04122090

Reaction notes

Loading…