Dichloromethane → Boc-Thz piperidine

HRID 2269644Notes

Reaction equation

HRID 2269644 reaction equation
C(Cl)Cl.[N:4]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][S:10][CH2:9][C@H:5]1[C:6]([OH:8])=[O:7].F[P-](F)(F)(F)(F)F.ClC1N(C)CC[NH+]1C.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(N(CC)CC)C>[N:4]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][S:10][CH2:9][C@H:5]1[C:6]([OH:8])=[O:7].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 218684192-Chloro-1,3-dimethylimidazolidin-1-ium;hexafluorophosphate

Product 1

HCID 131722960Boc-Thz piperidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a methylene chloride solution containing 300 mg of Boc-Thz-OH, 358 μl of triethylamine, 358 mg of 2-chloro-1, 3-dimethylimidazolidinium hexafluorophosphate and 153 μl of piperidine were added under ice cooling and the resultant mixture was stirred for 14 hr. The reaction mixture was treated similarly to that in Example 33 (Process 3) to give 300 mg of the title compound.

Workup

  1. additionwere added under ice cooling
  2. additionThe reaction mixture was treated similarly to that in Example 33 (Process 3)

Sources & evidence

ORD record
ord-4c5eb441d9bc4570877ded71086296d7
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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