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Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-butyl 4-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216923
Notes
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Reaction equation

HRID 216923 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:19][C:20]([C:22]1([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:2]([C@@H:3]([NH:19][C:20]([C:22]1([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:7][CH:6]=1)#[N:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568564(S)-tert-Butyl 4-(1-amino-3-(3'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568588(S)-tert-butyl 4-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(3′-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 8, step (i), 316 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (306 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and the solution was purified by chromatography on silica using ethyl acetate/isohexane and then ethyl acetate as eluent to afford the sub-titled compound as a white solid (282 mg).

Workup

  1. customThe solvent was partially evaporated
  2. customthe solution was purified by chromatography on silica

Sources & evidence

ORD record
ord-bf4e9b47d2c7465fbbc95e5b1390c0c8
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes