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

HRID 1379406Notes

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-ca954798cc334316b19847edb3c9b5ce
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05670675

Reaction notes

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