Ammonium Chloride → HCID 86597944, 화합물

HRID 854653

반응식

HRID 854653 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH:22]=O)[CH2:17]1.[NH2:24][C@H:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:26]([CH3:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>ClCCl.O.CC(O)=O>[CH3:27][CH:26]([CH3:28])[C@H:25]([NH:24][CH2:22][C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([O:15][CH2:14][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])[CH2:17]1)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 114626tert-Butyl L-valinateHCID 5049666Sodium triacetoxyborohydrideHCID 86597945cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexanecarbaldehyde

생성물 1

HCID 86597944HCID 86597944, 화합물수율 99%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

511 mg of cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexanecarbaldehyde, 0.9 ml of HOAc and 310 mg of tert-butyl (S)-valinate are dissolved in 5 ml of abs. dichloromethane. 500 mg of molecular sieve 4 Å are then added, and the suspension is cooled to 0° C. 414 mg of sodium triacetoxyborohydride are added a little at a time. This suspension is stirred at 0° C. for 2 h, 3 ml of saturated NH4Cl solution are then added and the suspension is stirred for a further 10 min. In each case 10 ml of water and dichloromethane are added, the phases are separated, the aqueous phase is extracted with dichloromethane and the combined organic phases are dried over MgSO4 and concentrated, which gives 760 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]-amino}butyrate. C28H42N2O4 (470.66); MS (ESI): 471.50 (MH+).

후처리

  1. addition500 mg of molecular sieve 4 Å are then added
  2. stirringthe suspension is stirred for a further 10 min
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialthe combined organic phases are dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-09f64f4ba2fe44ccb7115b1bf25fc90f
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259177B2

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