Acetic Anhydride → HCID 68771244, compound

HRID 1175114Notes

Reaction equation

HRID 1175114 reaction equation
Cl.[NH2:2][C:3]1([C:6]([NH:8][C@H:9]([B:14]2[O:18][C@@H:17]3[CH2:19][C@@H:20]4[CH2:23][C@H:22]([C@:16]3([CH3:26])[O:15]2)[C:21]4([CH3:25])[CH3:24])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH2:5][CH2:4]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:27]([NH:2][C:3]1([C:6]([NH:8][C@H:9]([B:14]2[O:18][C@@H:17]3[CH2:19][C@@H:20]4[CH2:23][C@H:22]([C@:16]3([CH3:26])[O:15]2)[C:21]4([CH3:24])[CH3:25])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH2:5][CH2:4]1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 68768788HCID 68768788, compound

Product 1

HCID 68771244HCID 68771244, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}cyclopropane-carboxamide hydrochloride (0.50 g, 1.30 mmol) in DMF (5.0 mL) was added acetic anhydride (0.15 g, 1.43 mmol). The reaction mixture was cooled to 0° C., and DIEA (0.34 g, 2.6 mmol) was added slowly over 1 h. The reaction was allowed to stir at 0° C. After 1.5 h, the reaction mixture was diluted with H2O (20 mL) and washed with EtOAc (2×30 mL). The organic layers were combined and washed with H2O (2×20 mL), dried over MgSO4, filtered, and concentrated to give the title compound (0.473 g, 93%). LC/MS: Rt=1.78 min, ES+391 (Formic Acid method).

Workup

  1. washwashed with EtOAc (2×30 mL)
  2. washwashed with H2O (2×20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f761a2401d6a484f989b00ca8507ce8b
Source dataset
uspto-grants-2010_11
Patent number
US07838673B2

Reaction notes

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