2-Mercaptoethanol → HCID 68618327, compound

HRID 1158483Notes

Reaction equation

HRID 1158483 reaction equation
[C:1]([O:5][C:6](=[O:41])[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17][N:18]([CH:31]([CH3:33])[CH3:32])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:15][N:14]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].SCCO.C1CCN2C(=NCCC2)CC1>CC#N>[C:1]([O:5][C:6](=[O:41])[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17][NH:18][CH:31]([CH3:33])[CH3:32])[CH2:15][N:14]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68616510((3S*,4R*)-1-benzyl-4-{[isopropyl-(2-nitro-benzenesulfonyl)-amino]-methyl}-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester

Product 1

HCID 68618327HCID 68618327, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ((3S*,4R*)-1-benzyl-4-{[isopropyl-(2-nitro-benzenesulfonyl)-amino]-methyl}-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester (8.9 g, 23.02 mmol), 2-mercaptoethanol (0.81 mL, 11.60 mmol), and DBU (0.79 mL, 5.27 mmol) in CH3CN (10 mL) is stirred for 2 h at room temperature. The mixture is concentrated and then diluted with Et2O and H2O. The organic layer is separated, and the aqueous phase is extracted 3 times with Et2O. The combined organic extracts are dried (MgSO4), and the solvent is concentrated to give the title compound which is used without further purification in the next step. TLC, Rf (AcOEt)=0.61. MS (LC-MS): 404.3 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.45 min.

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with Et2O and H2O
  3. customThe organic layer is separated
  4. extractionthe aqueous phase is extracted 3 times with Et2O
  5. dry with materialThe combined organic extracts are dried (MgSO4)
  6. concentrationthe solvent is concentrated

Sources & evidence

ORD record
ord-90a9452c074e4e5ba9eab8d2f2a3bc30
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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