2-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acid → Boc-Gly-Gly-Val-Pro-OH

HRID 973526Notes

Reaction equation

HRID 973526 reaction equation
[NH:1]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:14]([N:16]1[CH2:30][CH2:29][CH2:28][C@H:17]1[C:18]([O:20]CC1C=CC=CC=1)=[O:19])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:8])=[O:4].N(C(OC(C)(C)C)=O)CC(NCC(O)=O)=O>C(O)(=O)C>[NH:1]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:14]([N:16]1[CH2:30][CH2:29][CH2:28][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acidHCID 14306249Boc-Gly-Gly-Val-Pro-OBzl

Product 1

HCID 14306251Boc-Gly-Gly-Val-Pro-OH

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

IV (6.2 g, 0.012 mole) in acetic acid was hydrogenated and worked up as for II to obtain V quantitatively, no sharp m.p. 743 Calcd. for 83° C. Rf3, 0.25; Rf4, 0.15. Anal. Calcd. for C19H32N4O7 : C, 51.10; H, 7.67; N, 12.54%. Found: C, 51.28: H, 7.50, N, 12.38%.

Workup

  1. customto obtain V quantitatively
  2. customfor 83° C

Sources & evidence

ORD record
ord-5e25e1195be4490bb72f7cd56265aced
Source dataset
uspto-grants-1991_11
Patent number
US05064430

Reaction notes

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