Penicillamine → (3S)-2,2-Dimethyl-1,4-thiazinane-3-carboxylic acid

HRID 1976488Notes

Reaction equation

HRID 1976488 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[CH2:10]1CCN2C(=NCCC2)C[CH2:11]1.C[Si](Cl)(C)C>ClC(Cl)C.CN(C=O)C>[CH3:4][C:3]1([CH3:5])[S:6][CH2:11][CH2:10][NH:1][C@H:2]1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 5852PenicillamineHCID 6397ChlorotrimethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 11984304(3S)-2,2-Dimethyl-1,4-thiazinane-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a 0° suspension of 14.92 g (0.10 mmol) of D-penicillamine in 300 mL of dichloroethane and 2.0 mL of DMF was added 22.4 mL of DBU followed by 19.0 mL of trimethylsilyl chloride. The ice bath was removed and the reaction was stirred for 3h, after which an additional 29.9 mL of DBU was added. The reaction was stirred overnight at room temperature and then 10 mL of methanol was added and the reaction was stirred for 1h. The resulting white precipitate was filtered off, washed with 10 mL of methanol and dried in vacuo to provide 16 g of (3 S)-2,2-dimethyl-3-thiomorpholine carboxylic acid as a white solid.

Workup

  1. customThe ice bath was removed
  2. additionafter which an additional 29.9 mL of DBU was added
  3. stirringThe reaction was stirred overnight at room temperature
  4. addition10 mL of methanol was added
  5. stirringthe reaction was stirred for 1h
  6. filtrationThe resulting white precipitate was filtered off
  7. washwashed with 10 mL of methanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e1c1c891166042b880a36848460caff8
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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