1-Octanethiol → HCID 10189085, compound

HRID 489659Notes

Reaction equation

HRID 489659 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([C@@H:32]2[C@@H:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:35][CH2:34][N:33]2C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[O:31])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(S)CCCCCCC.N12CCCN=C1CCCCC2>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:29][C:30]([C@@H:32]2[C@@H:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:35][CH2:34][NH:33]2)=[O:31])[C:10]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:26])=[O:27])[CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69151496HCID 69151496, compound

Product 1

HCID 10189085HCID 10189085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

The title compound was prepared according to the procedure of Sheppeck, J. E., et al. (Tetrahedron Lett. 2000, 41, 5329-5333) using fluoren-9-ylmethyl 2-{N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl)piperidyl)-2-oxoethyl]carbamoyl}(2S, 3R)-3-phenylpyrrolidine carboxylate (Step a) (415 mg, 0.5 mmol), THF (10 mL), n-octanethiol (Aldrich) (876 mg, 6 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) (5 mg, 0.03 mmol). The reaction mixture was stirred for 5 h at 25° C. and the organic solvent was removed in vacuo. To the residue was added Et2O (20 mL) resulting in precipitation of the compound. The precipitate was collected by filtration and washed with hexane to provide a yellow solid. Purification by preparative reverse phase HPLC [Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 100% CH3CN (0.1% TFA) for 2 min] provided the title compound (TFA salt) as a white foam (187 mg). MS (ESI, pos. ion) m/z: 609 (M+1); (ESI, neg. ion) m/z: 607 (M−1). Calc'd for C32H37ClN4O4S: 608.22. Anal. Calcd for C32H37ClN4O4S.1.4C2HF3O2: C, 54.37; H, 5.03; N, 7.29. Found: C, 54.26; H, 5.19; N, 7.41.

Workup

  1. customThe title compound was prepared
  2. customthe organic solvent was removed in vacuo
  3. additionTo the residue was added Et2O (20 mL)
  4. customresulting in precipitation of the compound
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with hexane
  7. customto provide a yellow solid
  8. customPurification by preparative reverse phase HPLC [Phenomenex
  9. wait5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min

Sources & evidence

ORD record
ord-1183694195c847399a3d871bd066755f
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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