Hydrochloric Acid → (2S)-N-((1S,2S)-3-{(2S,3R)-2-[N-(tert-butyl)carbamoyl]-3-hydroxypyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamide

HRID 1780240ノート

反応式

HRID 1780240 の反応式
Cl.C(O[C:7]([N:9]1[CH2:20][CH2:19][C@@H:18]([O:21][Si](C(C)(C)C)(C)C)[C@H:10]1[C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:8])(C)(C)C.[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:45]([NH:47][C@@H:48]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C@H:49]([OH:53])C(O)=O)=[O:46])[CH2:41][C:42](=[O:44])[NH2:43])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1.CO>[CH2:29]([O:36][C:37]([NH:39][C@H:40]([C:45]([NH:47][C@@H:48]([CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C@H:49]([OH:53])[C:7]([N:9]1[CH2:20][CH2:19][C@@H:18]([OH:21])[C@H:10]1[C:11]([NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[O:8])=[O:46])[CH2:41][C:42](=[O:44])[NH2:43])=[O:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 22872710(3R)-1-t-butoxycarbonyl-N-t-butyl-3-t-butyldimethylsilyloxy-L-prolinamideHCID 57125825(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid

生成物 1

HCID 473132(2S)-N-((1S,2S)-3-{(2S,3R)-2-[N-(tert-butyl)carbamoyl]-3-hydroxypyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamide収率 41.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

1.5 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 50 mg (0.13 mmol) of (3R)-1-t-butoxycarbonyl-N-t-butyl-3-t-butyldimethylsilyloxy-L-prolinamide (prepared as described in Preparation 12) in 0.5 ml of methanol, and the mixture was stirred at room temperature for 1 hour. The solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with benzene. The excess hydrogen chloride was then removed by distillation as an azeotrope with the benzene. The resulting residue was dried in vacuo for 2 hours and the whole of the resulting (3E)-N-t-butyl-3-t-butyldimethylsilyloxy-L-prolinamide hydrochloride was reacted with 55 mg (0.13 mmol) of (2S,3S)-3-(N2 -benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid (prepared as described in Preparation 1) following a procedure similar to that described in Example 1, to obtain 33 mg of the title compound as a white powder, melting at 109°-112° C.

後処理

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was mixed with benzene
  3. customThe excess hydrogen chloride was then removed by distillation as an azeotrope with the benzene
  4. customThe resulting residue was dried in vacuo for 2 hours

出典と根拠

ORDレコード
ord-4974866c2f4c442fb06f2d9814afd204
出典データセット
uspto-grants-1997_05
特許番号
US05629406

反応ノート

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