Propyl mercaptan → HCID 67462595, compound

HRID 553837Notes

Reaction equation

[CH2:1]([SH:4])[CH2:2][CH3:3].[H-].[Na+].[CH2:7]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:45])[C@@H:19]([NH:29][C:30]([C:32]2[CH:37]=[C:36](Cl)[N:35]=[C:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:33]=2)=[O:31])[CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:13]1)=[O:11])[CH3:8].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:7]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:45])[C@@H:19]([NH:29][C:30]([C:32]2[CH:37]=[C:36]([S:4][CH2:1][CH2:2][CH3:3])[N:35]=[C:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:33]=2)=[O:31])[CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

1-propanethiol (11 μl) was added to a suspension of NaH (4 mg) in anhydrous DMF (0.3 ml) at 0° C. After 1 h stirring at 0° C., 4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (50 mg) dissolved in DMF (0.1 ml) was added. The mixture was allowed to warm to RT and was stirred at RT until completion. A NaHCO3 solution was added and the resulting mixture was extracted with DCM. The org. phases were dried (Na2SO4) and evaporated off. The crude was directly used in the next step.

Workup

additionwas added
temperatureto warm to RT
stirringwas stirred at RT until completion
extractionthe resulting mixture was extracted with DCM
dry with materialphases were dried (Na2SO4)
customevaporated off

Sources & evidence

ORD record: ord-74010be171fb4c4fa3b5a0cbeb2649c3
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048881B2

Reaction notes

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