Acetyl chloride → Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-(acetylamino)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2172996Notes

Reaction equation

HRID 2172996 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C@H:6]1[C@@H:11]2[C@@H:9]([C@H:10]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@:8]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:7]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(CC)CC)C>ClCCl.O>[C:1]([NH:5][C@H:6]1[C@@H:11]2[C@@H:9]([C@H:10]2[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C@:8]([NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:7]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86695979Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Product 1

HCID 86695980Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-(acetylamino)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylateYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (334.31 μL, 368.75 mg, 4.70 mmol) in dichloromethane (5 mL) is added to a stirring, cooled solution of di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.30 g, 3.91 mmol) and triethylamine (709.32 μL, 514.97 mg, 5.09 mmol) in dichloromethane (19.57 mL) at 0° C. then stirred. After 90 minutes, dilute with water and extract with dichloromethane (3×25 mL). The combined organic extracts are dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving the title compound (2.40 g, 3.81 mmol, 97%): MS (m/z): 653 (M+1).

Workup

  1. extractionextract with dichloromethane (3×25 mL)
  2. dry with materialThe combined organic extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efba7c9b4d464891ade544239345e943
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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