Diisopropylethylamine → HCID 480306, compound

HRID 429960Notes

Reaction equation

HRID 429960 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:9]([OH:20])[CH2:10][NH:11][CH2:12][C:13]([CH3:19])([CH3:18])[CH2:14][CH2:15][C:16]#[N:17])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:38]1[C:42]2[CH:43]=[CH:44][C:45]([S:47](Cl)(=[O:49])=[O:48])=[CH:46][C:41]=2[O:40][CH2:39]1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C@H:9]([OH:20])[CH2:10][N:11]([S:47]([C:45]1[CH:44]=[CH:43][C:42]2[O:38][CH2:39][O:40][C:41]=2[CH:46]=1)(=[O:48])=[O:49])[CH2:12][C:13]([CH3:19])([CH3:18])[CH2:14][CH2:15][C:16]#[N:17])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 49134011,3-Benzodioxole-5-sulfonyl chlorideHCID 21356821HCID 21356821, compound

Product 1

HCID 480306HCID 480306, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(1S,2R)-1-Benzyl-3-(4-cyano-2,2-dimethyl-butylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester (0.099 g, 0.25 mmol) was dissolved in CH2Cl2 and treated with diisopropylethylamine (0.066 ml, 0.38 mmol) and Benzo[1,3]dioxole-5-sulfonyl chloride (0.067 g, 0.31 mmol) at ambient temperature under argon with stirring. After 15 h the reaction mixture was concentrated in vacuo, taken up in EtOAc, washed with sat. aq. NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. Purification by column chromatography (1% MeOH in CH2Cl2) gave 0.083 g of a white solid. MS (ES): 574 (M+1).

Workup

  1. concentrationAfter 15 h the reaction mixture was concentrated in vacuo
  2. washwashed with sat. aq. NaHCO3, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customPurification by column chromatography (1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1c366d35456649c98e09cfa0c26ccc46
Source dataset
uspto-grants-2001_11
Patent number
US06319946B1

Reaction notes

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