反応 #1062991

ord-741de2c07a5f452484f69758833f102d

反応方程式

CC(C)(C)OC(=O)N[C@@H]1COc2ccccc2NC1=O
(R)-3-(tert-butoxycarbonyl-amino)-2,3-dihydro-1,5-benzoxazepin-4-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(C)OC(=O)N[C@H](CO)C(=O)O
N-Boc-(D)-serine
CC(C)c1ccc(CCl)cc1
p-isopropylbenzyl chloride
[I-].[K+]
potassium iodide
CC(C)(C)OC(=O)N[C@H]1COc2ccccc2NC1=O
(S)-3-(tert-butoxycarbonylamino)-2,3-dihydro-1,5-benzoxazepin-4-one
→
CC(C)c1ccc(CN2C(=O)[C@H](NC(=O)OC(C)(C)C)COc3ccccc32)cc1
(R)-3-(tert-Butoxycarbonylamino)-5-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-1,5-benzoxazepin-4-one

反応物

CC(C)(C)OC(=O)N[C@@H]1COc2ccccc2NC1=O
(R)-3-(tert-butoxycarbonyl-amino)-2,3-dihydro-1,5-benzoxazepin-4-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(C)OC(=O)N[C@H](CO)C(=O)O
N-Boc-(D)-serine
CC(C)c1ccc(CCl)cc1
p-isopropylbenzyl chloride
[I-].[K+]
potassium iodide
CC(C)(C)OC(=O)N[C@H]1COc2ccccc2NC1=O
(S)-3-(tert-butoxycarbonylamino)-2,3-dihydro-1,5-benzoxazepin-4-one

試薬

なし

溶媒

CCCCCC.CCOC(C)=O
hexane ethyl acetate

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他Obtained analogously to the directions in Example 1a)

実験手順

Obtained analogously to the directions in Example 1a) starting from 4.8 g of (R)-3-(tert-butoxycarbonyl-amino)-2,3-dihydro-1,5-benzoxazepin-4-one (prepared analogously to (S)-3-(tert-butoxycarbonylamino)-2,3-dihydro-1,5-benzoxazepin-4-one, starting from N-Boc-(D)-serine), 4.4 g of p-isopropylbenzyl chloride, 2.9 g of potassium carbonate and 166 mg of potassium iodide. Rf value (eluant: hexane/ethyl acetate 4:1): 0.33.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05610153uspto-grants-1997_03