Potassium Carbonate → HCID 67189729, compound

HRID 2355475Notes

Reaction equation

HRID 2355475 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.[Si:18]([O:25][CH:26]1[CH2:31][CH2:30][CH:29]([CH2:32][C@H:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:34][NH:35][CH3:36])[CH2:28][CH2:27]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>O.C(Cl)Cl>[Si:18]([O:25][CH:26]1[CH2:27][CH2:28][CH:29]([CH2:32][C@H:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:34][N:35]([CH3:36])[C:1]([O:3][CH2:4][CH2:5][Si:6]([CH3:7])([CH3:8])[CH3:9])=[O:10])[CH2:30][CH2:31]1)([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 59382970HCID 59382970, compound

Product 1

HCID 67189729HCID 67189729, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Solid Teoc-OSu (1.35 g, 5.25 mmol) was added to a two-phase solution of (S)-tert-butyl 1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-3-(methylamino)propan-2-ylcarbamate (2.0 g, 5.0 mmol), K2CO3 (0.75 g, 9.0 mmol) in H2O (6 ml) and CH2Cl2 (12 mL). The mixture was vigorously stirred for 2 h at rt. The product was extracted with CH2Cl2. The combined organic layers were washed with sat'd aq NaHCO3 and brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography to provide (S)-tert-butyl 1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamate (1.9 g, 3.49 mmol, 70% yield). 1H NMR (400 MHz, CD3OD): 0.05 (s, 15H), 0.87 (s, 9H), 1.40 (s, 9H), 1.69 (s, 3H), 2.96 (m, 3H), 3.40-3.52 (m, 1H), 3.81-3.92 (m, 1H), 4.12-4.29 (m, 2H). MS (E/Z): 545 (M+H+)

Workup

  1. extractionThe product was extracted with CH2Cl2
  2. washThe combined organic layers were washed with sat'd aq NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4f1d9f92ee234ebba34f2ec70dbdde68
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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