Dimethylformamide → HCID 86639842, compound

HRID 656256Notes

Reaction equation

HRID 656256 reaction equation
[C@H:1]1([NH:9][C:10]([CH:12]([CH:45]([CH3:47])[CH3:46])[CH2:13][CH:14]([OH:44])[CH:15]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:16][CH:17]([CH2:21][C:22]2[CH:30]=[C:29]3[C:25]([CH:26]=[CH:27][N:28]3[CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:24][CH:23]=2)[CH:18]([CH3:20])[CH3:19])=[O:11])[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.ClS([N:52]=[C:53]=O)(=O)=O.CN(C)C=O>ClCCl>[C:53]([C:26]1[C:25]2[C:29](=[CH:30][C:22]([CH2:21][CH:17]([CH:18]([CH3:19])[CH3:20])[CH2:16][CH:15]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:42])[CH3:41])[CH:14]([OH:44])[CH2:13][CH:12]([C:10](=[O:11])[NH:9][C@H:1]3[C:3]4([CH2:4][CH2:5][O:6][CH2:7][CH2:8]4)[CH2:2]3)[CH:45]([CH3:47])[CH3:46])=[CH:23][CH:24]=2)[N:28]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[CH:27]=1)#[N:52]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 86639843HCID 86639843, compound

Product 1

HCID 86639842HCID 86639842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 mmol of tert-butyl (4-((R)-(6-oxaspiro[2.5]-oct-1-yl)carbamoyl)-2-hydroxy-1-(2-[1-(3-methoxypropyl)-1H-indol-6-ylmethyl]-3-methylbutyl)-5-methylhexyl)carbamate in 15 ml of dichloromethane is mixed with 1.5 mmol of chlorosulphonyl isocyanate and stirred at room temperature for 16 hours. 2 ml of N,N-dimethylformamide are added, and the reaction mixture is again stirred for 2 hours. It is quenched with water, and the suspension is vigorously stirred for 10 minutes. It is poured into 1M sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is identified by means of the Rf from the residue by flash chromatography (SiO2 60 F).

Workup

  1. stirringthe reaction mixture is again stirred for 2 hours
  2. customIt is quenched with water
  3. stirringthe suspension is vigorously stirred for 10 minutes
  4. additionIt is poured into 1M sodium bicarbonate solution
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried with sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-3b9ce8dfc30543d7ad70589ddf5f118c
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

Loading…