Triethylamine → HCID 23648597, compound

HRID 601977Notes

Reaction equation

HRID 601977 reaction equation
[NH2:1][C@H:2]([CH2:13][O:14][CH:15]([F:17])[F:16])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(OCC)(=O)C>[CH2:6]([NH:5][C:3](=[O:4])[C@H:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:13][O:14][CH:15]([F:16])[F:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68418816HCID 68418816, compound

Product 1

HCID 23648597HCID 23648597, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2R)-2-amino-N-benzyl-3-(difluoromethoxy)propanamide (113 mg, 0.46 mmol) in ethyl acetate was cooled in an ice bath. To the cooled solution was added triethylamine (139 mg, 1.38 mmol) followed by methanesulfonylchloride (63 mg, 0.55 mmol). The reaction mixture was stirred for 15 minutes and then quenched with water, extracted with ethyl acetate and washed with brine. The organic layer was dried, concentrated and triturated with diethyl ether to give the product (33 mg, 22%) as a white solid. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.31 (m, 5H), 6.73 (br, 1H), 6.24 (t, 1H), 5.21 (d, 1H), 4.48 (d, 2H), 4.21 (m, 3H), 3.01 (s, 3H)

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-993f8a039e9e445a8e8aa88b6b44140e
Source dataset
uspto-grants-2011_03
Patent number
US07902401B2

Reaction notes

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