Dicyclohexylcarbodiimide → HCID 11834249, compound

HRID 1828061Notes

Reaction equation

HRID 1828061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[SH:38]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([S:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=1)=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 178418616HCID 178418616, compound

Product 1

HCID 11834249HCID 11834249, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 12.9 g (56.51 mmol) of 1 and 17.49 g (84.77 mmol) of 1,3-dicyclohexylcarbodiimide in CH2Cl2 (250 mL) was added 9.42 g (84.77 mmol) of pyridine-2-thiol followed by 0.25 g (0.2 mmol) of 4-dimethylaminopyridine, and the mixture was stirred for 16 hrs at ambient temperature. The slurry was filtered and the resulting organic phase was evaporated to yield a yellow oil which was subject to column chromatography (EtOAc/Hexanes, 3:2) to yield 11.2 g (61.5%) of 2 as a yellow oil. TLC Rf=0.6 (EtOAc/Hexanes, 3:2)

Workup

  1. filtrationThe slurry was filtered
  2. customthe resulting organic phase was evaporated
  3. customto yield a yellow oil which

Sources & evidence

ORD record
ord-b4cb78a4a96e4be39e746d08150f959f
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

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