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

HRID 847643

반응식

HRID 847643 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 1NMR spectrum was consistent with the assigned structure. Analysis calculated for C36H47N3O6 : C, 69.99; H, 7.67; N, 6.80. Found: C, 69.26; H, 7.52; N, 6.61.

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-654c606790264998895c6be050f5cfa7
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05142056

연결된 노트

불러오는 중…