Ammonia → tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate

HRID 500015노트

반응식

HRID 500015 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C@@H:13]([OH:29])[CH2:14][C@H:15]([C:19](=[O:28])[NH:20][CH2:21][C:22]([C:25](=[O:27])[NH2:26])([CH3:24])[CH3:23])[CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10]([CH:30]([CH3:32])[CH3:31])[C@@H:9]1[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])[CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N.[Li].[Cl-].[NH4+]>O1CCCC1.C(O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:12]([CH2:11][C@H:10]([CH2:9][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])[CH:34]=1)[CH:30]([CH3:32])[CH3:31])[C@@H:13]([OH:29])[CH2:14][C@H:15]([C:19](=[O:28])[NH:20][CH2:21][C:22]([C:25](=[O:27])[NH2:26])([CH3:23])[CH3:24])[CH:16]([CH3:17])[CH3:18])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 11998976HCID 11998976, 화합물

생성물 1

HCID 53348234tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 0.037 g of amide 12 is dissolved in 1 mL of tetrahydrofurane and cooled to −78° C. Liquid ammonia is added followed by 0.0042 g of lithium metal. The deep blue solution is stirred for 2 hours at −78° C., and then 0.35 g of ethanol is added and the mixture is stirred for 30 minutes at −78° C. Ammonium chloride (0.15 g) is added and the mixture is warmed to room temperature. The organic phase is partitioned between water and ethyl acetate. The organic phase is separated and the solvent removed in vacuum. The residue is stirred with heptane and filtered. Removal of the heptane produces 13 identical with an authentic sample. M++H=652

후처리

  1. stirringthe mixture is stirred for 30 minutes at −78° C
  2. temperaturethe mixture is warmed to room temperature
  3. customThe organic phase is partitioned between water and ethyl acetate
  4. customThe organic phase is separated
  5. customthe solvent removed in vacuum
  6. stirringThe residue is stirred with heptane
  7. filtrationfiltered
  8. customRemoval of the heptane

출처 및 근거

ORD 기록
ord-b182b95923df444ab9c555312d15ff6e
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767831B2

반응 노트

불러오는 중…