Triethylamine → N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane

HRID 843285ノート

反応式

HRID 843285 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:10]([OH:13])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C.CCCCCCC>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C@@H:10]([OH:13])[CH2:11][O:12][S:22]([CH3:21])(=[O:24])=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 31297Methanesulfonyl chlorideHCID 11076870(2R,3S)-3-(t-butoxycarbonyl)amino-4-phenyl-butane-1,2-diol

生成物 1

HCID 10904464N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane収率 106.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-butanol 65.42 g(Net.63.38 g)dissolved in ethyl acetate 320 ml were added isopropyleter 320 ml, and then methane sulfonylchloride 28.3 g under ice-cooling, and triethylamine 25.0 g, successively, and the solution was stirred for 1 hr. N-heptane was added to the reaction solution and the solution was stirred for further 1 hr to deposit crystals, which were filtered and dried in vacuum to obtain the crude N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane 89.3 g (Net.55.7 g). The crude crystals. A ratio of main components in the crude crystals, which contain triethylamine hydrochloride, is the diol derivative compound:the 2-sulfonate derivative:the 1-sulfonate derivtive(the object product):the 1,2-disulfonate compound=1.3:0.1:95.4:3.2. A part of the crude crystal was dissolved in ethyl acetate, washed with water, and purified by recrystallization from ethyl acetate and isopropylether. The purified recrystals were used for anlysyses.

後処理

  1. additionwere added isopropyleter 320 ml
  2. filtrationwere filtered
  3. customdried in vacuum

出典と根拠

ORDレコード
ord-97c2f05933844521aeedba0bc5c9947d
出典データセット
uspto-grants-2002_04
特許番号
US06376685B1

反応ノート

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