Acetyl chloride → HCID 59598512, compound

HRID 2266290Notes

Reaction equation

HRID 2266290 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C@@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1)[C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)Cl>[C:40]([NH:1][CH2:2][CH2:3][O:4][C@@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1)[C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59598463HCID 59598463, compound

Product 1

HCID 59598512HCID 59598512, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round-bottom flask were added (R)-tert-butyl 2-((S)-(2-aminoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)morpholine-4-carboxylate (280 mg, 0.63 mmol), triethylamine (0.19 mL, 1.89 mmol) and anhydrous CH2Cl2 (15 mL). The mixture was cooled in an ice bath and a solution of acetyl chloride (49.2 mg, 0.045 mL, 0.63 mmol) was added. The reaction mixture was allowed to warm slowly to rt and stirred until the reaction was complete (ca 1˜2 h). The solvent was removed by evaporation, and the residue was purified by preparative tlc to give (R)-tert-butyl 2-((S)-(2-acetamidoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)morpholine-4-carboxylate (202 mg, 66%). 1H NMR (300 MHz, CDCl3): δ=1.45 (s, 9 H), 1.93 (s, 3 H), 2.38 (s, 3 H), 2.87˜3.2 (m, 6 H), 3.32˜3.92 (m, 5 H), 4.28 (d, 1 H), 7.01˜7.25 (m, 3 H), 7.28˜7.37 (m, 4 H), 9.41-9.54 (s, 1 H). MS (E/Z): 487 (M+H+)

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. custom(ca 1˜2 h)
  3. customThe solvent was removed by evaporation
  4. customthe residue was purified by preparative tlc

Sources & evidence

ORD record
ord-cc5d96249d3342f4a2276990a2f25d73
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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