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Potassium Carbonate → 2-(Trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamate

HRID 1254319
Notes
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Reaction equation

HRID 1254319 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:5][C:6]1([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+].[C:30]([O:39]N1C(=O)CCC1=O)([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=O>C1COCC1.O>[OH:12][C:6]1([CH2:5][CH:4]([NH:13][S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:3][N:2]([CH3:1])[C:30](=[O:39])[O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:37])[CH3:38])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 593830731-(3-(Methylamino)-2-(tosylamino)propyl)cyclohexanol

Product 1

HCID 671912342-(Trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamateYield 74%

Reagents, catalysts & solvents 1

HCID 21881883
Oxolane--water (1/1)
Solvent

Procedure

To a solution of 1-(3-(methylamino)-2-(tosylamino)propyl)cyclohexanol in 3:1 THF/H2O v/v (4 mL) was added K2CO3 (240 mg, 1.74 mmol), followed by Teoc-OSu (248 mg, 0.96 mmol). The resulting solution was stirred at rt for 30 min and the organic solvent was removed under reduced pressure. The residue was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried, filtered and concentrated under vacuum. The residue was chromatographied on silica gel to give 2-(trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamate (300 mg, 74% for two steps). MS m/z 469 (M+H+).

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. extractionThe residue was extracted with EtOAc (2×)
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6fbe0079871f4dd0adf832d44d77fdd8
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455521B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes