Hydrochloric Acid → (R)-2-amino-2-ethoxycarbonylsuccinimide Hydrochloride

HRID 57750Notes

Reaction equation

HRID 57750 reaction equation
C(OC([NH:8][C@:9]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][C:13](=[O:15])[NH:12][C:10]1=[O:11])=O)(C)(C)C.[ClH:21]>C(OCC)(=O)C>[ClH:21].[NH2:8][C@:9]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][C:13](=[O:15])[NH:12][C:10]1=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66725143(R)-2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinimide

Product 1

HCID 66725247(R)-2-amino-2-ethoxycarbonylsuccinimide HydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-2-t-Butyloxycarbonylamino-2-ethoxycarbonylsuccinimide (380 mg) obtained in Example 16 was dissolved in a 4 mol/L solution of hydrochloric acid in ethyl acetate (8 mL), and the reaction mixture was stirred for 1 hour, and then concentrated under reduced pressure. The residue was suspended in ether and filtered to obtain the title compound (288 mg, yield: 97%) as white crystals. Optical rotation [α]D25 was −14.8° (c 1.0, methanol). Optical purity was 75.6% ee.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a76446c5f1d148ba8bcc224c54623770
Source dataset
uspto-grants-2016_09
Patent number
US09434737B2

Reaction notes

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