Water → (1S,2R,3S,4S,5R,6R)-2-amino-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid

HRID 2173000Notes

Reaction equation

HRID 2173000 reaction equation
C(OC([NH:8][C@@:9]1([C:33]([O:35]C(C)(C)C)=[O:34])[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[C@@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([O:28]C(C)(C)C)=[O:27])=O)(C)(C)C.O>C(O)(=O)C>[NH2:8][C@@:9]1([C:33]([OH:35])=[O:34])[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[C@@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 962WaterHCID 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-dicarboxylate

Product 1

HCID 57338826(1S,2R,3S,4S,5R,6R)-2-amino-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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 (5.30 g, 9.01 mmol) is added to water (30.02 mL) and acetic acid (30.02 mL). Heat the reaction at reflux until the complete consumption of the starting material. Cool and concentrate on a rotary evaporator. Triturate the concentrate with diethyl ether, collect the precipitate, then dry in a vacuum oven to give the title compound (3.30 g, 8.77 mmol, 97%). MS (m/z): 376/378 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureat reflux until the complete consumption of the starting material
  4. temperatureCool
  5. concentrationconcentrate on a rotary evaporator
  6. customTriturate the
  7. concentrationconcentrate with diethyl ether
  8. customcollect the precipitate
  9. customdry in a vacuum oven

Sources & evidence

ORD record
ord-df8131086b034e6c816ca402fdf12ed4
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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