Acetic Anhydride → HCID 86691261, compound

HRID 2037286Notes

Reaction equation

HRID 2037286 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@@:9]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:14][C:13](=[O:15])[C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C>ClCCl>[C:1]([NH:8][C@@:9]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:14][C:13](=[O:15])[C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11322807HCID 11322807, compound

Product 1

HCID 86691261HCID 86691261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetic acid anhydride (5 mL, 50.8 mmol) to a stirred solution of diethyl (1S,2S,5R,6R)-2-amino-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (7.2 g, 28.2 mmol) and triethylamine (7.9 mL, 56.4 mmol) in dry dichloromethane (72 mL) at room temperature. After 2 hours, quench with water (100 mL) and stir vigorously for 20 minutes. Separate the dichloromethane layer via a hydrophobic frit and evaporate to a light brown oil (9.6 g). Purify by flash chromatography eluting with ethyl acetate:iso-hexane (70:30 to 90:10) to give the title compound as a pale yellow glass foaming on drying (6.53 g, 22 mmol). MS (m/z): 298 (M+1), 320 (M+23), 617 (2M+23).

Workup

  1. customquench with water (100 mL)
  2. customSeparate the dichloromethane layer via a hydrophobic frit
  3. customevaporate to a light brown oil (9.6 g)
  4. customPurify by flash chromatography
  5. washeluting with ethyl acetate:iso-hexane (70:30 to 90:10)

Sources & evidence

ORD record
ord-9744a243dd5646c2b835a271b6956748
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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