Sodium Hydroxide → 2,5-Di-(N-(Cbz-isoleucinyl)amino)-3,4dihydroxy-1,6-diphenylhexane

HRID 1078130

반응식

HRID 1078130 반응식
[NH2:1][C@H:2]([C@@H:10]([OH:22])[C@H:11]([OH:21])[C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+](C1C=CC(O[C:33](=[O:50])[C@H:34]([C@H:46]([CH2:48][CH3:49])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=CC=1)([O-])=O.[OH-:51].[Na+]>O1CCCC1>[C:36]([NH:35][C@H:34]([C:33]([NH:1][CH:2]([CH:10]([OH:22])[CH:11]([OH:21])[CH:12]([NH:20][C:33](=[O:50])[C@H:34]([C@H:46]([CH2:48][CH3:49])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:50])[C@H:46]([CH2:48][CH3:49])[CH3:47])([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:51]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 2063382N-[(Phenylmethoxy)carbonyl]-L-isoleucine 4-nitrophenyl esterHCID 10990240(2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

생성물 1

HCID 228455822,5-Di-(N-(Cbz-isoleucinyl)amino)-3,4dihydroxy-1,6-diphenylhexane수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 10 mg (0.033 mmol) of the resultant compound of Example 171 and 38.6 mg (0.10 mmol) of Cbz-isoleucine p-nitrophenyl ester in 0.2 ml of tetrahydrofuran was stirred at ambient temperature for 21 h. The resulting misture was diluted with 1 ml of tetrahydrofuran, treated with 0.5 ml of 3N NaOH, stirred for 45 min, extracted with chloroform, washed sequentially with 3N NaOH and saturated brine, dried over MgSO4, and concentrated. The residue was purified on silica gel by eluting with 2% methanol in chloroform to provide 23 mg (86%) of the desired compound. Mass spectrum: (M+H)+ =795.

후처리

  1. stirringstirred for 45 min
  2. extractionextracted with chloroform
  3. washwashed sequentially with 3N NaOH and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washby eluting with 2% methanol in chloroform

출처 및 근거

ORD 기록
ord-dab3ee642ec246688805674ab5838dcf
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05545750

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