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

HRID 216966Notes

Reaction equation

HRID 216966 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:26][C:27]([C:29]1([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][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:26][C:27]([C:29]1([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([S:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)(=[O:19])=[O:18])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568573(S)-tert-Butyl 4-(1-amino-3-(4'-(morpholinosulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 59568591(S)-tert-Butyl 4-(1-cyano-2-(4'-(morpholinosulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4′-(morpholinosulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 27, step (i), 0.24 g) in dichloromethane (10 mL) was treated with Burgess' reagent (0.185 g) and the mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1) to afford the sub-titled compound (210 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1)

Sources & evidence

ORD record
ord-8d3edc69837b43fe88bcc137aefb2f1a
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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