Hydrochloric Acid → 2-{[(Tert-butoxy)carbonyl](cyclopropyl)amino}acetic acid

HRID 1278914Notes

Reaction equation

C([O:3][C:4](=[O:10])[CH2:5][NH:6][CH:7]1[CH2:9][CH2:8]1)C.BrC[C:13]([O:15]CC)=[O:14].[CH:18]1(N)[CH2:20][CH2:19]1.Cl.[CH3:23]O>>[C:13]([N:6]([CH:7]1[CH2:8][CH2:9]1)[CH2:5][C:4]([OH:3])=[O:10])([O:15][C:20]([CH3:18])([CH3:19])[CH3:23])=[O:14]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 7748Ethyl bromoacetate

HCID 69828Cyclopropylamine

HCID 22476174Glycine, N-cyclopropyl-, ethyl ester

Product 1

HCID 224761182-{[(Tert-butoxy)carbonyl](cyclopropyl)amino}acetic acid

Procedure

Boc-N-Cyclopropylglycine was prepared from N-cyclopropylglycine ethyl ester, ethyl bromoacetate and cyclopropylamine (similar to J. W. Skiles et al., J. Med. Chem. 35 (1992) 641) and then converted under standard conditions into the Boc-protected form, then hydrolyzed with MeOH/2N NaOH and finally acidified with 1N HCl.

Sources & evidence

ORD record: ord-c0769fa3706c47dabb93415d783154bf
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444817B1

Reaction notes

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