N-Carbobenzoxy-L-valine → HCID 3011050, compound

HRID 1078139Notes

Reaction equation

[NH2:1][CH:2]([C:6]([F:16])([F:15])[CH:7]([OH:14])[CH:8]([NH2:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH:3]([CH3:5])[CH3:4].[NH:17]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C@H:18]([C:22](O)=[O:23])[CH:19]([CH3:21])[CH3:20]>>[C:25]([NH:17][C@H:18]([C:22]([NH:1][CH:2]([C:6]([F:15])([F:16])[CH:7]([OH:14])[CH:8]([NH:13][C:22](=[O:23])[C@H:18]([CH:19]([CH3:21])[CH3:20])[NH:17][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH:3]([CH3:4])[CH3:5])=[O:23])[CH:19]([CH3:21])[CH3:20])([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]

Participants

Reactant 2

HCID 726987N-Carbobenzoxy-L-valine

HCID 22910286HCID 22910286, compound

Product 1

HCID 3011050HCID 3011050, compoundYield 56%

Procedure

Using the procedure described in Example 182, the product from Example 263 was coupled to Cbz-Val to give the desired compound (56%). Mass spectrum: (M+H)+ =705. 1H NMR (CDCl3) δ0.82 (m, 12H), 3.90 (m, 1H), 4.02 (m, 1H), 4.30 (m, 1H), 4.55 (m, 1H), 5.02 (s, 4H), 5.80 (br d, 1H), 7.20 (br d, 1H), 7.35 (m, 10H), 7.70 (br d, 1H).

Sources & evidence

ORD record: ord-e4f8b403c4904529bb52a52301b6dc16
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05545750

Reaction notes

Loading…