Formic Acid → HCID 59619232, compound

HRID 1367548Notes

Reaction equation

HRID 1367548 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:28][O:29][C:30](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:8])[CH2:5][CH2:4]1)#[N:2].C(O)=[O:50]>>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([C@H:12]2[CH2:11][C@@H:10]([CH2:28][O:29][CH:30]=[O:50])[C@H:9]([C:7](=[O:8])[NH:6][C:3]3([C:1]#[N:2])[CH2:4][CH2:5]3)[CH2:13]2)(=[O:16])=[O:15])=[C:18]([C:24]([F:26])([F:27])[F:25])[CH:19]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 66918641(1R,2R,4S)-4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-2-trityloxymethyl-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Product 1

HCID 59619232HCID 59619232, compoundYield 25%

Procedure

A mixture of (1R,2R,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-trityloxymethyl-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 152 step 7, 10 mg) in concentrated formic acid (0.2 mL) was stirred at room temperature during 1.5 h. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogenocarbonate. The organic layer was washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane:ethyl acetate (3:1 to 1:1 v/v) as eluant to afford the title compound (2 mg, 25%) as a colorless oil. MS (EI): 524 (M)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane:ethyl acetate (3:1 to 1:1 v/v) as eluant

Sources & evidence

ORD record
ord-fd55ce3f06df4138b6babac033916f09
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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