Methyl N-(triethylammoniosulfonyl)carbamate → HCID 86675095, compound

HRID 216983Notes

Reaction equation

HRID 216983 reaction equation
CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[NH2:16][C:17](=O)[C@@H:18]([NH:37][C:38]([C:40]1([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)=[O:39])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[CH2:34][N:33]([CH3:35])[C:32](=[O:36])[C:29]3=[N:30][CH:31]=2)=[CH:22][CH:21]=1>ClCCl>[C:17]([C@@H:18]([NH:37][C:38]([C:40]1([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:51])([CH3:50])[CH3:52])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)=[O:39])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[CH2:34][N:33]([CH3:35])[C:32](=[O:36])[C:29]3=[N:30][CH:31]=2)=[CH:22][CH:21]=1)#[N:16]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68431036HCID 68431036, compound

Product 1

HCID 86675095HCID 86675095, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Burgess' reagent (348 mg) was added to (S)-tert-butyl 1-(1-amino-3-(4-(6-methyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)cyclohexylcarbamate (Example 32, step (iii), 391 mg) in dichloromethane (25 mL) at 20° C. under nitrogen. The resulting solution was stirred at room temperature for 16 h. The reaction mixture was diluted with dichloromethane, and washed with water. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by chromatography on silica eluting with methanol/ethyl acetate (10:90 to 40:60) to afford the sub-titled compound (360 mg).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by chromatography on silica eluting with methanol/ethyl acetate (10:90 to 40:60)

Sources & evidence

ORD record
ord-bb0d878654f64ec6b1167e8e514e6c91
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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