5-Methylthiophene-2-carboxylic acid → HCID 54022822, compound

HRID 1982624Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:3][S:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH3:17][C:18]1[S:22][C:21]([C:23](O)=[O:24])=[CH:20][CH:19]=1.ON1C2C=CC=CC=2N=N1>>[CH3:15][CH:14]([CH3:16])[CH2:13][C@H:2]([NH:1][C:23]([C:21]1[S:22][C:18]([CH3:17])=[CH:19][CH:20]=1)=[O:24])[CH2:3][S:4][CH2:5][C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

Reactant 3

HCID 747135-Methylthiophene-2-carboxylic acid

HCID 757711-Hydroxybenzotriazole

HCID 54147463HCID 54147463, compound

Product 1

HCID 54022822HCID 54022822, compoundYield 14.4%

Procedure

3.00 g (0.012 mol) of (S)-1,1-dimethylethyl [(2-amino-4-methylpentyl)thio]acetate, 172 g (0.012 mol) 5-methyl-2-thiophene carboxylic acid, 1.64 g (0.012 mol) 1-hydroxybenzotriazole, and 2.50 g (0.012 mol) N,N-dicyclohexylcarbodiimide are reacted according to the procedure for Example 3 to give 0.64 g of (S)-1,1-dimethylethyl [[4-methyl-2-[[[5-methyl-2-thienyl]carbonyl]amino]pentyl]thio]acetate as a crystalline solid, mp 81°-83°; [α]D25 +56.5° (C 0.63, methanol).

Sources & evidence

ORD record: ord-c41c9d52d90a4c2aa60629bda0e2dde0
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04596819

Reaction notes

Loading…