Acetoxyacetyl chloride → HCID 86695981, compound

HRID 2172998Notes

Reaction equation

HRID 2172998 reaction equation
[C:1]([O:4][CH2:5][C:6](Cl)=[O:7])(=[O:3])[CH3:2].[NH2:9][C@H:10]1[C@@H:15]2[C@@H:13]([C@H:14]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C@:12]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@@H:11]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:1]([O:4][CH2:5][C:6]([NH:9][C@H:10]1[C@@H:15]2[C@@H:13]([C@H:14]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C@:12]([NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@@H:11]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 86695982HCID 86695982, compound

Product 1

HCID 86695981HCID 86695981, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetoxyacetyl chloride (0.116 mL, 1.08 mmol) to a solution of diethyl (1S,2R,3R,4S,5R,6S)-4-amino-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.47 g, 0.89 mmol) and diisoproylethylamine (0.32 mL, 1.83 mmol) in dichloromethane (9 mL) at room temperature. After 2.5 hours, wash the solution with saturated NaHCO3 (2×), brine (1×), dry over MgSO4, filter, and conc. under reduced pressure. Purify by flash chromatography eluting with a gradient of 0 to 100% ethyl acetate in hexanes over 30 min. to yield the title compound as a white solid (0.43 g, 0.68 mmol, 76%). MS (m/z): 531 (M+H-BOC).

Workup

  1. washwash the solution with saturated NaHCO3 (2×), brine (1×)
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. customPurify by flash chromatography
  5. washeluting with a gradient of 0 to 100% ethyl acetate in hexanes over 30 min.

Sources & evidence

ORD record
ord-228de43d230d42088f1da48b5e5f56b0
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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