Benzylamine → HCID 23648567, compound

HRID 601976Notes

Reaction equation

HRID 601976 reaction equation
C(O[C:6]([NH:8][C@H:9]([CH2:13][O:14][CH:15]([F:17])[F:16])[C:10]([OH:12])=O)=[O:7])(C)(C)C.[CH2:18](N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1.C(OCC)(=O)C>[C:6]([NH:8][C@H:9]([CH2:13][O:14][CH:15]([F:16])[F:17])[C:10]([NH:40][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:12])(=[O:7])[CH3:18]

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 57539230HCID 57539230, compound

Product 1

HCID 23648567HCID 23648567, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-[(tert-butoxycarbonyl)amino]-3-(difluoromethoxy)propanoic acid (197 mg, 1.0 mmol) and triethylamine (303 mg, 3 mmol) in THF (10 mL) at −78° C., isobutyl chloroformate (174 mg, 1.28 mmol) was added dropwise. After 30 minutes, benzylamine (161 mg, 1.5 mmol) was added and the reaction mixture allowed to warm up to room temperature. The mixture then was diluted with ethyl acetate and washed with water, 0.5N HCl and Brine. The organic layer was dried over magnesium sulphate, concentrated, and triturated with ether-hexanes (1:3) to give (2R)-2-(acetylamino)-N-benzyl-3-(difluoromethoxy)propanamide (48 mg, 16.7%) as a white solid. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.25-7.39 (m, 5H), 6.68 (w, 1H), 6.42 (d, 1H), 6.24 (wt, 1H), 4.73 (m, 1H), 4.48 (d, 2H), 4.24 (dd, 1H), 4.01 (dd, 1H) and 2.05 (s, 3H).

Workup

  1. washwashed with water, 0.5N HCl and Brine
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. concentrationconcentrated
  4. customtriturated with ether-hexanes (1:3)

Sources & evidence

ORD record
ord-301ab1180b2742a29e1c9cc0a0241784
Source dataset
uspto-grants-2011_03
Patent number
US07902401B2

Reaction notes

Loading…