Water → HCID 70272687, compound

HRID 1420459Notes

Reaction equation

HRID 1420459 reaction equation
[CH:1]([C:4]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:25](=[O:27])[NH2:26])[N:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[C:6]1=[O:24])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:37][C:38]([O:40]C(C)(C)C)=[O:39].O>CN(C)C=O>[CH:1]([C:4]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:25](=[O:27])[NH2:26])[N:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13]([C:15]2[N:16]([CH2:37][C:38]([OH:40])=[O:39])[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[C:6]1=[O:24])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 131721211HCID 131721211, compound

Product 1

HCID 70272687HCID 70272687, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of example 46 (1.200 g) under nitrogen in anhydrous dimethylformamide (10 mL) at 0°-5° C. was added sodium hydride (60% dispersion in mineral oil, 0.113 g). After stirring until the reaction mixture was homogeneous, tert-butyl bromoacetate (0.434 mL) was added. The reaction mixture was maintained at 0°-5° C. for 1.5 h and then added to water (100 mL). The resulting slurry was cooled to 0°-5° C., filtered and the filter cake was dried under high vacuum to provide the title compound as an off-white solid (1.482 g). MS(ESI): [M+H]+ =561.2. 1H NMR (300 MHz, CDCl3) d=1.07 (d, J=6.8 Hz, 6H), 1.47-2.20 (m, 6H), 1.56 (s, 9H), 3.17 (m, 1H), 3.64-3.77 (m, 2H), 3.85 (d, J=16.6 Hz, 1H), 4.75 (m, 1H), 4.98 (m, 1H), 5.27 (m, 2H), 7.01 (b, 1H), 7.13 (m, 1H): 7.19-7.31 (m, 3H), 7.41-7.50 (m, 4H), 7.63 (m, 1H), 7.71 (m, 1H).

Workup

  1. temperatureThe reaction mixture was maintained at 0°-5° C. for 1.5 h
  2. temperatureThe resulting slurry was cooled to 0°-5° C.
  3. filtrationfiltered
  4. customthe filter cake was dried under high vacuum

Sources & evidence

ORD record
ord-0ed37a7d39b14668bc58623d9355074b
Source dataset
uspto-grants-1999_03
Patent number
US05889182

Reaction notes

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