Acetone → HCID 86594364, compound

HRID 351377Notes

Reaction equation

HRID 351377 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:15][C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[C:9]2=[O:28])[C@H:4]([CH2:29][S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)[O:40][C:41](C)=O.[Na+].[CH3:53][C:54]([CH3:56])=O.[CH2:57]=[O:58]>C(Cl)Cl.CC(O)=O.CCOC(C)=O>[F:24][C:23]([F:26])([F:25])[C:57]([OH:40])=[O:58].[CH:54]([N:1]([CH3:41])[C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:15][C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[C:9]2=[O:28])[C@H:4]([CH2:29][S:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)(=[O:32])=[O:31])[CH2:3]1)([CH3:56])[CH3:53]

Participants

8

Reactant 4

HCID 180AcetoneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69034636HCID 69034636, compound

Product 1

HCID 86594364HCID 86594364, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[(3S)-1-(1S,2R,4R)-(4-amino-2-benzenesulfonylmethyl-cyclohexyl)-2-oxo-azepan-3-yl]-3-trifluoromethyl-benzamide (30 mg) in CH2Cl2 (15 mL) at rt was added NaBH(OAc)3 (50 mg), acetone (2 mL), and three drops of AcOH. After 2 h, formaldehyde (2 mL) was added and the solution was stirred for another 2 h. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3, water, and brine. The organic layer was dried, filtered, and concentrated to afford to a crude oil which was purified by semi-preparative HPLC to give the title compound. MS [M+H]+32 608.

Workup

  1. washwashed with saturated NaHCO3, water, and brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford to a crude oil which
  6. customwas purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-156530b1f13542b095a9e6846638a411
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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