Acetic Acid → HCID 58459344, compound

HRID 2036637Notes

Reaction equation

HRID 2036637 reaction equation
[NH2:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:24])[C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].CC(O)=O.[CH:29]1([CH:32]=O)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCOC(C)=O>[CH:29]1([CH2:32][NH:1][C:2]2[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[NH:12][C:13](=[O:24])[C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH3:15])[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58459276Carbamic acid, N-[(1S)-2-[[2-amino-3-(methylsulfonyl)phenyl]amino]-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 58459344HCID 58459344, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)-tert-butyl 1-(2-amino-3-(methylsulfonyl)phenylamino)-1-oxopropan-2-ylcarbamate (prepared in example 51) (440 mg, 1.23 mmol), glacial AcOH (0.43 mL, 7.4 mmol) and cyclopropanecarbaldehyde (0.18 mL, 2.5 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (780 mg, 3.7 mmol) and stirred at rt under N2 for 18 h. The reaction mixture was diluted with EtOAc, washed with water, sat. aq sodium bicarbonate solution, brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel column using 10 to 20% gradient of EtOAC:DCM (1:1) in DCM as eluent to give (S)-tert-butyl 1-(2-(cyclopropylmethylamino)-3-(methylsulfonyl)phenylamino)-1-oxopropan-2-ylcarbamate: LC-MS (ESI) m/z 412.1 [M+H]+.

Workup

  1. washwashed with water, sat. aq sodium bicarbonate solution, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel column

Sources & evidence

ORD record
ord-3b64b44cf45543e6bb5d2030a08b9c89
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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