4,5-Dibromothenoic acid → (R)-3-{[(4,5-dibromo-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1162662Notes

Reaction equation

HRID 1162662 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[Br:15][C:16]1[CH:17]=[C:18]([C:22](O)=[O:23])[S:19][C:20]=1[Br:21]>>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C@H:3]([CH2:2][NH:1][C:22]([C:18]2[S:19][C:20]([Br:21])=[C:16]([Br:15])[CH:17]=2)=[O:23])[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 806114,5-Dibromothenoic acidHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 58748268(R)-3-{[(4,5-dibromo-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

58.1 Using general procedure E, (R)-3-aminomethyl-1-N-tert-butoxycarbonyl-pyrrolidine was coupled with 4,5-dibromothiophene-2-carboxylic acid to give (R)-3-{[(4,5-dibromo-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. White solid. MS 466.9 ([M−H]−)

Sources & evidence

ORD record
ord-e5498dce60a24e78a8cd61da59d0c890
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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