1-Octanethiol → HCID 66854592, compound

HRID 1970459Notes

Reaction equation

HRID 1970459 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:42])[C@@H:13]([NH:24]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(S)CCCCCCC.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:42])[C@@H:13]([NH2:24])[CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66856580HCID 66856580, compound

Product 1

HCID 66854592HCID 66854592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.71 g 4-[(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyryl]-piperazine-1-carboxylic acid ethyl ester in 30 ml THF was stirred in the presence of 8.9 ml 1-octanethiol and 101 μl DBU. After 12 h the mixture was concentrated, the residue dissolved in dichloromethane and extracted with 0.1 M HCl. The aqueous phase was brought to pH 9 by adding aqueous NaHCO3 before being extracted with dichloromethane. The product was obtained after evaporation of the solvent and was used in the subsequent reaction. Yield: 2.27 g colorless foam.

Workup

  1. concentrationAfter 12 h the mixture was concentrated
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionextracted with 0.1 M HCl
  4. additionby adding aqueous NaHCO3
  5. extractionbefore being extracted with dichloromethane
  6. customThe product was obtained
  7. customafter evaporation of the solvent
  8. customwas used in the subsequent reaction

Sources & evidence

ORD record
ord-417a4f72e70140d2ae5ceb64d2d3908a
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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