Potassium Carbonate → Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2173010Notes

Reaction equation

HRID 2173010 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C@@:15]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[C@@H:19]([O:31]C(C2C=CC([N+]([O-])=O)=CC=2)=O)[C@@H:18]2[C@H:16]1[C@H:17]2[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:13])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([O:11][C:12]([NH:14][C@@:15]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[C@@H:19]([OH:31])[C@@H:18]2[C@H:16]1[C@H:17]2[C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86695973Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-{[(4-nitrophenyl)carbonyl]oxy}bicyclo[3.1.0]hexane-2,6-dicarboxylate

Product 1

HCID 86695974Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylateYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (153.45 g, 1.11 mol) is added to a suspension of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-{[(4-nitrophenyl)carbonyl]oxy}bicyclo[3.1.0]hexane-2,6-dicarboxylate (273.00 g, 370.11 mmol) in methanol (3.28 L) at ambient temperature. After 16 hours, the reaction is concentrated in vacuo. The residue is dissolved in methyl tert-butyl ether (2 L), and washed subsequently with water (0.8 L), brine (0.8 L), dried over MgSO4, and concentrated in vacuo to yield the title compound as a white solid (215 g, 98% yield).

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. dissolutionThe residue is dissolved in methyl tert-butyl ether (2 L)
  3. washwashed subsequently with water (0.8 L), brine (0.8 L)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-455f2610e26449ff8485aab6bce0a8d1
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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