Triethylamine → 2-(t-Butyloxycarbonylamino)-4-(N-(Cbz-isoleucyl)amino)-1,5-diphenyl-3-hydroxypentane

HRID 1379409

반응식

HRID 1379409 반응식
[NH2:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:3]([OH:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+](C1C=CC([O:37][C:38](=O)[C@H:39]([C@H:51]([CH2:53][CH3:54])[CH3:52])[NH:40][C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=CC=1)([O-])=O.C(N(CC)CC)C>C1COCC1.[OH-].[Na+].C(Cl)(Cl)Cl.CO>[C:16]([O:15][C:13]([NH:12][CH:4]([CH:3]([OH:20])[CH:2]([NH:1][C:38](=[O:37])[C@H:39]([C@H:51]([CH2:53][CH3:54])[CH3:52])[NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 2063382N-[(Phenylmethoxy)carbonyl]-L-isoleucine 4-nitrophenyl esterHCID 147043774-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

생성물 1

HCID 228456432-(t-Butyloxycarbonylamino)-4-(N-(Cbz-isoleucyl)amino)-1,5-diphenyl-3-hydroxypentane수율 81%

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 6212Chloroform용매4회HCID 8028Tetrahydrofuran용매2회HCID 14798Sodium Hydroxide용매

실험 절차

The resultant compound of Example 11 (125 mg, 0.34 mmol), N-benzyloxycarbonyl-isoleucine p-nitrophenyl ester (196 mg, 0.51 mmol) and triethylamine (94 μL, 0.67 mmol) were combined with 1.0 mL of dry THF and stirred together at ambient temperature overnight. The reaction mixture was then heated at reflux temperature for 3 h. The cooled reaction mixture was then diluted with 5 mL of THF and 5 mL of 3M aqueous sodium hydroxide solution was added. The mixture was stirred at ambient temperature for approximately 0.5 h. and was then diluted with chloroform. The chloroform solution was washed with 3×25 mL of 0.5M aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (227 mg) was taken up in approximately 5 mL of chloroform and applied to a 1.0×45 cm column of 40 mesh silica gel. The column was eluted @ 5-10 p.s.i. sequentially with 100 mL of chloroform, 100 mL of 0.5% methanol in chloroform and 100 mL of 1% methanol in chloroform to give 169 mg (81% yield) of the title compound; FAB MS M/Z: 618 (M+H)+. The 300 MHz 1H NMR spectrum was consistent with the assigned structure.

후처리

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux temperature for 3 h
  3. customThe cooled reaction mixture
  4. additionwas added
  5. stirringThe mixture was stirred at ambient temperature for approximately 0.5 h.
  6. washThe chloroform solution was washed with 3×25 mL of 0.5M aqueous sodium hydroxide solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe column was eluted @ 5-10 p.s.i

출처 및 근거

ORD 기록
ord-a6c6bd8b2bd44cc0a4b5939114f93be8
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670675

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