Methyl N-(triethylammoniosulfonyl)carbamate → HCID 59568545, compound

HRID 216937Notes

Reaction equation

HRID 216937 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][C:14]([F:17])=[C:13]([F: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][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568617HCID 59568617, compound

Product 1

HCID 59568545HCID 59568545, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(3′,4′-difluorobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 13, step (i), 305 mg) in dichloromethane (10 mL) was treated with Burgess' reagent (289 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and the residue was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1) to yield the sub-titled compound (239 mg).

Workup

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

Sources & evidence

ORD record
ord-ebff42d76f9640848c963765fee48d39
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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