Dimethylformamide → HCID 18704233, compound

HRID 2288292Notes

Reaction equation

HRID 2288292 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]1([CH2:30][O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:15](=[O:16])[N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=2)[C:13](=[O:29])[NH:12]1.CN(C)[CH:40]=[O:41]>>[C:4]([O:41][CH2:40][C:6]#[C:7][CH2:8][N:12]1[C:11]([CH2:10][O:9][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][O:3]2)([CH2:30][O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:15](=[O:16])[N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:26])[F:27])[CH:18]=2)[C:13]1=[O:29])(=[O:3])[CH3:5]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 18704226HCID 18704226, compound

Product 1

HCID 18704233HCID 18704233, compound

Procedure

416 mg of 50% sodium hydride and dropwise 4 g of the product obtained in Stage 5 of Example 1 and 15 ml of dimethylformamide are introduced and the resultant mixture is rinsed with 1 ml of dimethylformamide. 10 minutes after the end of the release of hydrogen, 3.2 g of 4-bromo-2-butyne-1-ol acetate prepared as described in J. W. Lown GENE 149, 81 (1994) and 2 ml of dimethylformamide are added, and rinsing is carried out with 0.5 ml of dimethylformamide. After one hour 30 minutes, the reaction medium is poured into 100 ml of water containing 0.5 g of monopotassium phosphate, extraction is carried out 4 times with ether, the organic phase is washed with water and with salt water and dried. Purification is carried out by chromatography on silica eluting with methylene chloride-acetone: 95-5 and 4.47 g of expected product (orange resin) is obtained.

Workup

  1. washthe resultant mixture is rinsed with 1 ml of dimethylformamide
  2. custom10 minutes after the end of the release of hydrogen, 3.2 g of 4-bromo-2-butyne-1-ol acetate prepared
  3. washrinsing
  4. additionthe reaction medium is poured into 100 ml of water containing 0.5 g of monopotassium phosphate, extraction
  5. washthe organic phase is washed with water and with salt water
  6. customdried
  7. customPurification

Sources & evidence

ORD record
ord-636bf2178698492eb8a920b75347567c
Source dataset
uspto-grants-2000_07
Patent number
US06087509

Reaction notes

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