Hydrochloric Acid → HCID 17959240, compound

HRID 1761039Notes

Reaction equation

HRID 1761039 reaction equation
C([O:3][C:4](=[O:19])[CH:5]([NH:16]C=O)[C:6]([SH:15])([CH3:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])C.Cl.[Cl:21]CCl.CO>C(O)(=O)C>[ClH:21].[NH2:16][CH:5]([C:6]([SH:15])([CH3:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:4]([OH:19])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6344DichloromethaneHCID 12051595HCID 12051595, compound

Product 1

HCID 17959240HCID 17959240, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16.7 g of 2-formylamino-3-mercapto-3-methyldecanoic acid ethyl ester as a 6:4 threo/erythro mixture (product 6) were added at room temperature to 606 ml of 6N hydrochloric acid and then stirred for 24 hours under reflux (TLC check: dichloromethane:methanol:glacial acetic acid 35:5:3). After cooling to room temperature the reaction mixture was stirred further while cooling with ice. The precipitated white solid was suction filtered, washed with ether and then dried in vacuo. 13.3 g (94.9% of theory) of rac-2-amino-3-mercapto-3-methyldecanoic acid hydrochloride were thus obtained as a 6:4 threo/erythro mixture (compound 6; product 1).

Workup

  1. stirringwas stirred further
  2. temperaturewhile cooling with ice
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-643e478bf4124cffbdbcf806c4cba8cc
Source dataset
uspto-grants-2005_01
Patent number
US06846843B2

Reaction notes

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