Glycine → HCID 131711384, compound

HRID 2163175Notes

Reaction equation

[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([N:8]1[CH2:39][CH2:38][CH2:37][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][C:25]([O:27][C:28]1[CH:36]=[CH:35][C:31]([N+:32]([O-:34])=[O:33])=[CH:30][CH:29]=1)=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].NCC(O)=O.N[C@H](C(O)=O)C(C)C.[F:60][C:61]([F:66])([F:65])[C:62]([OH:64])=[O:63]>>[NH2:1][C@H:2]([C:6]([N:8]1[CH2:39][CH2:38][CH2:37][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][C:25]([O:27][C:28]1[CH:29]=[CH:30][C:31]([N+:32]([O-:34])=[O:33])=[CH:35][CH:36]=1)=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:4])[CH3:5].[F:60][C:61]([C:62]([OH:64])=[O:63])([F:66])[F:65]

Participants

Reactant 4

HCID 750Glycine

HCID 6287L-Valine

HCID 6422Trifluoroacetic acid

HCID 131711386HCID 131711386, compound

Product 1

HCID 131711384HCID 131711384, compound

Procedure

Boc-Val-Pro-Gly-Val-Gly-ONp (3.2 g, 4.93 mmol) prepared as described in Urry et al. (1975) J. Mol. Biol. 96, pp. 101-117, was dissolved in 99% trifluoroacetic acid (6 ml) and the mixture was treated in the same manner as described for the preparation of XI in part (j); yield 3.1 g (95%), m.p. 122-127° C., Rf1 0.13, Rf3 0.42. Calcd. for C27H37N6O10F3.1/2H2O: C, 48.29; H, 5.70; N, 12.51%. Found: C, 48.00; H, 5.86; N, 12.21%. Amino acid analysis: Pro, 1.00; Gly, 1.90; Val, 2.09.

Workup

additionthe mixture was treated in the same manner

Sources & evidence

ORD record: ord-93a169c2fc274a828d911f955a060e69
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04132746

Reaction notes

Loading…