2-Thiophenecarbonyl chloride → HCID 22879068, compound

HRID 2293455Notes

Reaction equation

HRID 2293455 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:25])[C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:18][C@@H:19]([NH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32]>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:25])[C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:18][C@@H:19]([NH:24][C:31]([C:27]2[S:26][CH:30]=[CH:29][CH:28]=2)=[O:32])[CH2:20][CH:21]([CH3:22])[CH3:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 22873003HCID 22873003, compound

Product 1

HCID 22879068HCID 22879068, compoundYield 55%

Procedure

Using the procedure described in Example 7, treatment of 1-[2-(S)-amino-4-methylpentyl]-L-proline 4-phenylbutylamide (113 mg) with 2-thiophenecarbonyl chloride (50 uL) provided 74 mg (55%) of the title compound. The 1H NMR and Mass spectrum analysis of this compound was consistent with the structure. Rf=0.46 (EtOAc). LSIMS=456; (mass calculated for C26H37N3O2S=455.60).

Sources & evidence

ORD record
ord-12be590191854d99ad9bb5b2835c145f
Source dataset
uspto-grants-1997_11
Patent number
US05686469

Reaction notes

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