Butyryl chloride → HCID 9831299, 화합물

HRID 1291793노트

반응식

HRID 1291793 반응식
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:7][C@H:8]([C@@H:30]([NH:38][C:39](=[O:49])[C@H:40]([CH:46]([CH3:48])[CH3:47])[NH:41][C:42]([O:44][CH3:45])=[O:43])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][N:10]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[NH:11][C:12](=[O:22])[C@H:13]([CH:19]([CH3:21])[CH3:20])[NH:14][C:15]([O:17][CH3:18])=[O:16]>CN(C1C=CN=CC=1)C.O1CCOCC1.N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:7][C@H:8]([C@@H:30]([NH:38][C:39](=[O:49])[C@H:40]([CH:46]([CH3:48])[CH3:47])[NH:41][C:42]([O:44][CH3:45])=[O:43])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:9][N:10]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[NH:11][C:12](=[O:22])[C@H:13]([CH:19]([CH3:20])[CH3:21])[NH:14][C:15]([O:17][CH3:18])=[O:16])(=[O:5])[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 2

HCID 8855Butyryl chloride3회HCID 461993methyl N-[(1S)-1-[[(1S,2S)-1-benzyl-3-[cyclohexylmethyl-[[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]amino]amino]-2-hydroxy-propyl]carbamoyl]-2-methyl-propyl]carbamate2회

생성물 1

HCID 9831299HCID 9831299, 화합물

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매2회HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

50 μ(0.495 mmol) of butyric acid chloride and 2 mg (0.017 mmol) of DMAP are added to an ice-cooled mixture of 200 mg (0.33 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(methoxy-carbonyl)-(L)-valyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[N-methoxycarbonyl-(L)-valyl]-hydrazine (Example 73a) in 2.6 ml of dioxane and 0.4 ml of pyridine. After 18 h at RT, according to HPLC there is still 1-[2(S)-hydroxy-3(S)-(N-(methoxycarbonyl)-(L)-valyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[N-methoxycarbonyl-(L)-valyl]-hydrazine present in the reaction mixture, and therefore a further 0.75 equivalents of butyric acid chloride and a few granules of DMAP are added. After a further 18 h, a 3rd portion of 1.5 equivalents of butyric acid chloride is added and the mixture is further stirred for one night at RT (→HPLC: fully reacted). The reaction mixture is diluted with ethyl acetate and washed with 2 portions of saturated NaHCO3 solution, water and brine, the aqueous phases are extracted twice with ethyl acetate, and the organic phases are dried with Na2SO4 and concentrated by evaporation. Digestion of the oily residue from hexane in an ultrasound bath yields the pure title compound: TLC Rf (O)=0.67; tRet (V)=17.2 min; FAB-MS (M+H)+ =676.

후처리

  1. temperaturecooled
  2. waitAfter a further 18 h
  3. customfully reacted)
  4. washwashed with 2 portions of saturated NaHCO3 solution, water and brine
  5. extractionthe aqueous phases are extracted twice with ethyl acetate
  6. dry with materialthe organic phases are dried with Na2SO4
  7. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-49a7c985d1b1438d81253e47454f8ead
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753652

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