Methanol → 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 2172990Notes

Reaction equation

HRID 2172990 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(OCC)(=O)C>[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

5

Reactant 3

HCID 887MethanolHCID 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 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (5.11 g, 36.60 mmol) is added to a solution 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 (9.00 g, 12.20 mmol) and methanol (122.01 mL, 3.01 moles), and then stirred at room temperature. After 1 hour, dilute the reaction mixture with ethyl acetate, wash with water (75 mL), brine (75 mL), dry over sodium sulfate, and concentrate under reduced pressure to give a residue. The residue is purified by flash chromatography, eluting with 10-60% ethyl acetate:hexanes to give the title compound (5.3 g, 9.01 mmol, 74%). MS (m/z): 610/612 (M+1).

Workup

  1. washwash with water (75 mL), brine (75 mL)
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. customto give a residue
  5. customThe residue is purified by flash chromatography
  6. washeluting with 10-60% ethyl acetate

Sources & evidence

ORD record
ord-a7c2d2f15fe24322886b6d8df8b3caaa
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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