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

HRID 216945Notes

Reaction equation

HRID 216945 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18]#[N:19])[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:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18]#[N:19])[CH:12]=2)=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568611(S)-tert-Butyl 4-(1-amino-3-(3'-cyano-4'-methylbiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568559(S)-tert-Butyl 4-(1-cyano-2-(3'-cyano-4'-methylbiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(3′-cyano-4′-methylbiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 18, step (i), 154 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (145 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and the mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1) to afford the sub-titled compound (127 mg).

Workup

  1. customThe solvent was partially evaporated
  2. customthe mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1)

Sources & evidence

ORD record
ord-511794996dd44379ac3413d7181e3d40
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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