Hydrochloric Acid → HCID 57144254, compound

HRID 1976422Notes

Reaction equation

HRID 1976422 reaction equation
[OH-].[Na+].[NH2:3][C@@H:4]([C:9]([OH:11])=[O:10])[C:5]([SH:8])([CH3:7])[CH3:6].Br[CH2:13][CH2:14][CH2:15][OH:16].Cl>C(O)C>[NH2:3][C@H:4]([C:5]([S:8][CH2:13][CH2:14][CH2:15][OH:16])([CH3:7])[CH3:6])[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5852PenicillamineHCID 123083-Bromo-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 57144254HCID 57144254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2N sodium hydroxide (11.3 mL, 22.7 mmol) was added to D-(−)-penicillamine (2.5 g, 16.8 mmol) at 0° C. Once all the solid was dissolved, a solution of 3-bromopropanol (3.03 g, 21.8 mmol) in ethanol (17 mL) was slowly added at 0° C. and the resulting mixture was stirred for 15 h at room temperature. The mixture was treated with 1N hydrochloric acid until pH is ˜6 and the solvents were removed to obtain (2S)-2-amino-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoic acid as a white solid. This solid was used for the next step without further purification; Electrospray Mass Spec 208.1 (M+H)+

Workup

  1. dissolutionOnce all the solid was dissolved
  2. customthe solvents were removed

Sources & evidence

ORD record
ord-e8a60af9618840e788933fbfee3711d2
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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