Water → HCID 67190138, compound

HRID 2355342Notes

Reaction equation

HRID 2355342 reaction equation
[C:1]([O:10]N1C(=O)CCC1=O)([O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7])=O.[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[CH2:27][NH:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[Na+].[Na+].O>C(Cl)Cl>[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:33][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[CH2:27][N:28]([CH2:29][CH2:30][CH2:31][CH3:32])[C:1]([O:3][CH2:4][CH2:5][Si:6]([CH3:7])([CH3:8])[CH3:9])=[O:10])=[O:24])([CH3:19])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 57544575HCID 57544575, compound

Product 1

HCID 67190138HCID 67190138, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Solid Teoc-OSu (390 mg, 1.5 mmol) was added to a vigorously stirred 2-phase mixture of (2S)-2-(tert-butoxycarbonylamino)-1-butylamino-3-cyclohexylpropane (312.8 mg, 1.0 mmol), Na2CO3 (525 mg, 5.0 mmol), H2O (5.0 mL), and CH2Cl2 (25.0 mL). The mixture was stirred for 90 min at rt and the reaction was taken up in CH2Cl2 (50 mL), washed with brine (3×10 mL), dried over Na2SO4, decanted, and stripped to give a clear oil. This oil was separated on a 4 g SiO2 column to give crude (2S)-2-(tert-butoxycarbonylamino)-1-(N-butyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-cyclohexylpropane (486.5 mg, 106%) as a clear oil (quant). MS ESI+ve m/z 479 (M+Na). The crude product was used without further purification.

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. customto give a clear oil
  5. customThis oil was separated on a 4 g SiO2 column

Sources & evidence

ORD record
ord-a089577e41cf450295bb35e16992ad04
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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