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

HRID 1863467Notes

Reaction equation

HRID 1863467 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][NH:5][C:6](=[O:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH-].[Na+].Cl>O1CCCC1.O>[C:12]([O:11][C:9]([NH:8][CH2:7][C:6]([NH:5][CH2:4][C:3]([OH:17])=[O:2])=[O:16])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 637608methyl N-(tert-butoxycarbonyl)glycylglycinate

Product 1

HCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add, to a solution of t-butoxycarbonyl-glycyl-glycine methyl ester (3.9 g.) in tetrahydrofuran (30 ml.) and water (30 ml.), 16 ml. of 1 N sodium hydroxide dropwise. Stir the mixture until homogenous (1 1/2 hours), then acidify to pH 3 with dilute hydrochloric acid and evaporate to dryness. Suspend the residue in acetone, filter and evaporate the filtrate to dryness to afford the title product (m.p. 125°-128° C.).

Workup

  1. customevaporate to dryness
  2. filtrationfilter
  3. customevaporate the filtrate to dryness

Sources & evidence

ORD record
ord-710803a182684b609a8ef982c035b471
Source dataset
uspto-grants-1979_09
Patent number
US04169141

Reaction notes

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