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Dichloromethane → Boc-Thz piperidine

HRID 427379
Notes
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Reaction equation

HRID 427379 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8471
Triethylamine
Solvent

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-d066e1fdd2f74086b0887d4cb7e2a1b1
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313094B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes