Hydrochloric Acid → HCID 23563668, compound

HRID 1058993Notes

Reaction equation

HRID 1058993 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([C:10]([O:12]C)=[O:11])[C@H:7]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C@@H:6]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:4].[OH-].[Li+].O.Cl>CO>[C:23]([O:22][C:20]([NH:19][C@H:6]1[C@@H:7]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:10]([OH:12])=[O:11])[CH2:9][C@@H:5]1[C:3]([OH:4])=[O:2])=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 70029755HCID 70029755, compound

Product 1

HCID 23563668HCID 23563668, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-(1S,2S,3R,4R)-2-(t-Butyloxycarbonylamino)-3-(acetamidomethyl)-cyclopentane-1,4-dicarboxylic acid dimethyl ester (255 mg, 0.68 mmole) and lithium hydroxide (2.2 equivalents) in 15 mL of 4:1 methanol:water were reacted at room temperature for 2 hours. The reaction was acidified with dilute HCl and extracted with ethyl acetate (3×60 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated to provide the title compound.

Workup

  1. extractionextracted with ethyl acetate (3×60 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1bedfd026a714d2dbaa7c3f93cf7d2a2
Source dataset
uspto-grants-2003_02
Patent number
US06518305B1

Reaction notes

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