Diisopropylethylamine → HCID 480319, compound

HRID 2074942Notes

Reaction equation

HRID 2074942 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:4]([OH:26])[CH2:5][N:6]([CH2:18][C:19]([CH3:25])([CH3:24])[CH2:20][CH2:21][C:22]#[N:23])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8].C(N(C(C)C)CC)(C)C.[C:43](=O)([O:51]C1C=CC([N+]([O-])=O)=CC=1)[O:44][CH:45]1[CH2:50][O:49][CH2:48][O:47][CH2:46]1>C(Cl)Cl>[O:47]1[CH2:46][CH:45]([O:44][C:43](=[O:51])[NH:2][C@@H:3]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@H:4]([OH:26])[CH2:5][N:6]([CH2:18][C:19]([CH3:25])([CH3:24])[CH2:20][CH2:21][C:22]#[N:23])[S:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)(=[O:8])=[O:9])[CH2:50][O:49][CH2:48]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 154296011,3-Dioxan-5-yl 4-nitrophenyl carbonateHCID 21356815HCID 21356815, compound

Product 1

HCID 480319HCID 480319, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2R,3S)-(3-Amino-2-hydroxy-4-phenyl-butyl)-N-(4-cyano-2,2-dimethyl-butyl)-4-methoxy-benzenesulfonamide hydrochloride (0.111 g, 0.22 mmol) was dissolved in CH2Cl2 and treated with diisopropylethylamine (0.120 ml, 0.67 mmol) and 1,3-dioxan-5-yl 4-nitrophenyl carbonate (0.066 g, 0.25 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% to 3% MeOH in CH2Cl2) gave 0.084 g of a white solid. MS (ES): 590 (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% to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9cfe684c1e9e4b26982401abea84878e
Source dataset
uspto-grants-2011_04
Patent number
US07919523B2

Reaction notes

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