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 500015ノート

反応式

HRID 500015 の反応式
[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]

参加物

7

反応物 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 11998976HCID 11998976、化合物

生成物 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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-b182b95923df444ab9c555312d15ff6e
出典データセット
uspto-grants-2010_08
特許番号
US07767831B2

反応ノート

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