Hydrochloric Acid → HCID 86584394, compound

HRID 1356394Notes

Reaction equation

HRID 1356394 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:18][CH2:19][C@H:20]([S:22][CH2:23][C@@:24]([CH3:29])([C:26]([OH:28])=[O:27])[NH2:25])[CH3:21])=O)C1C=CC=CC=1.[ClH:30]>>[ClH:30].[NH2:18][CH2:19][C@H:20]([S:22][CH2:23][C@@:24]([CH3:29])([C:26]([OH:28])=[O:27])[NH2:25])[CH3:21]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69516015HCID 69516015, compound

Product 1

HCID 86584394HCID 86584394, compound

Procedure

The product of Example-3C, S-[(1R)-2-(Benzyloxycarbonylamino)-1-methylethyl]-2-methyl-L-cysteine trifluoroacetate, (0.5 g, 1.14 mmol) was dissolved in 6N HCl and refluxed for 1.5 hour. The mixture was then cooled to room temperature and extracted with EtOAc. The aqueous layer was concentrated in vacuo to give the title product, (2R, 5R)—S—(1-amino-2-propyl)-2-methyl-cysteine hydrochloride (0.29 g), which was used without further purification. 1H NMR (H2O, 400 MHz) δ 1.2 (m, 3H), 1.4 (m, 3H), 2.7 (m, 1H), 2.8-3.2 (m, 2H), 3.4 (m, 1H). (some doubling of peaks due to rotameric forms). MS m/z (electrospray): 193 [M+H+] (61%), 176 (53), 142 (34), 134 (100), and 102 (10).

Workup

  1. temperaturerefluxed for 1.5 hour
  2. extractionextracted with EtOAc
  3. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-b115e63fdf974192924351cfe96776f4
Source dataset
uspto-grants-2003_07
Patent number
US06586474B2

Reaction notes

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