Hydrochloric Acid → HCID 178457456, 화합물

HRID 2169209노트

반응식

HRID 2169209 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:37]([CH3:39])[CH3:38])[C:12]([C:14]1[NH:15][C:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Br:36])=[N:17][C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:37]([CH3:39])[CH3:38])[C:12]([C:14]1[NH:15][C:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Br:36])=[N:17][C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 178457490HCID 178457490, 화합물

생성물 1

HCID 178457456HCID 178457456, 화합물수율 34.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (69) (0.75 g, 1.22 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (10 ml). HCl (915 μl, 1.83 mmol, Eq: 1.5) was added and the resulting mixture was stirred at room temperature. After 30 minutes the solvent was mostly removed. The residue was partitioned between ethyl acetate and 1M NaOH. The aqueous layer was washed with ethyl acetate, the organic layers were washed with brine, combined, dried over Na2SO4, filtered and concentrated. The remaining brown oil was triturated in ethyl acetate/ether. The solid was collected by filtration, washed with a little ethyl acetate and dried to afford 5-benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (70) (0.21 g, 420 μmol, 34.4% yield) as an off-white solid. The mother liquor also showed clean product (0.43 g, 68% yield) of brown solid.

후처리

  1. customAfter 30 minutes the solvent was mostly removed
  2. customThe residue was partitioned between ethyl acetate and 1M NaOH
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe remaining brown oil was triturated in ethyl acetate/ether
  9. filtrationThe solid was collected by filtration
  10. washwashed with a little ethyl acetate
  11. customdried

출처 및 근거

ORD 기록
ord-d52a6b1f671a47bf8edf7339d822ff56
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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