Ammonium Chloride → HCID 69427531, compound

HRID 1006798Notes

Reaction equation

[CH2:1]([NH:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:33][N:34]=[N+]=[N-])=[O:7])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].[NH4+].[Cl-]>C(O)C>[CH2:1]([NH:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:10][C@H:9]1[CH2:33][NH2:34])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

275 mg (0.55 mmol) (2S,4R)-2-azidomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butylamide in 8 ml ethanol was treated with 83 mg (2.2 mmol) NaBH4 at 80° C. for 18 h. Additional 175 mg (4.6 mmol) NaBH4 were added in portions, and the reaction was stirred at 80° C. until no starting material could be detected. The solution was poured into a saturated NH4Cl solution, and was extracted with EtOAc, the organic phase was washed with brine, dried over Na2SO4 and evaporated. Column chromatography yielded 213 mg (82%) (2S,4R)-2-aminomethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butylamide as white foam, which was directly subjected to the following reactions according to reductive amination with 2,5-difluoro-benzaldehyde (example 4a) and subsequent trityl cleavage (method 3) yielding (2S,4R)-2-[(2,5-difluoro-benzylamino)-methyl]-4-mercapto-pyrrolidine-1-carboxylic acid butylamide as colorless oil, MS:358 (MH+).

Workup

extractionwas extracted with EtOAc
washthe organic phase was washed with brine
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-54b577cbef9d44dbbd63c027debd4581
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790860B2

Reaction notes

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