Methyl N-(triethylammoniosulfonyl)carbamate → HCID 59568626, compound

HRID 216933Notes

Reaction equation

HRID 216933 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:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:15]=3[CH:25]=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])[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1)=[O:28])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:15]=3[CH:25]=2)=[CH:9][CH:10]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568553HCID 59568553, compound

Product 1

HCID 59568626HCID 59568626, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4-(3-(3-methoxypropyl)-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 11, step (iii), 151 mg) in dichloromethane (10 mL) was treated with Burgess' reagent (121 mg) and the mixture was stirred for 18 h at room temperature. The solvent was partially evaporated and the mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1) to yield the sub-titled compound (137 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-0c9cdb831bb04a8f82244743a095afc0
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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