Benzylamine → HCID 57539234, compound

HRID 601971Notes

Reaction equation

HRID 601971 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][O:14][CH:15]([F:17])[F:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(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>[CH2:33]([NH:40][C:10](=[O:12])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][O:14][CH:15]([F:17])[F:16])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

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

Product 1

HCID 57539234HCID 57539234, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-[(tert-butoxycarbonyl)amino]-3-(difluoromethoxy)propanoic acid (510 mg, 2.0 mmol) and triethylamine (607.1 mg, 6 mmol) in THF (10 mL) at −78° C., isobutyl chloroformate (348 mg, 2.55 mmol) was added dropwise. After 30 minutes, benzylamine (321.5 mg, 3.0 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 tert-butyl {(1R)-2-(benzylamino)-1-[(difluoromethoxy)methyl]-2-oxoethyl}carbamate (345 mg, 50%) as a white solid. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.40-7.80 (m, 5H), 6.60 (t, 1H), 6.22 (wt, 1H), 5.25 (w, 1H), 4.32-4.55 (m, 4H), 4.05 (dd, 1H) and 1.48 (s, 9H).

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-891aaaa8a33c48879c87a59c62277fbb
Source dataset
uspto-grants-2011_03
Patent number
US07902401B2

Reaction notes

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