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4-Methylmorpholine → t-Butyl (6R,7R)-7-Amino-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate

HRID 1421804
ノート
印刷プレビュー

反応式

HRID 1421804 の反応式
C1(CC([NH:10][C@@H:11]2[C:30](=[O:31])[N:13]3[C:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:15]([CH:18]4[CH2:22][CH2:21][O:20][CH2:19]4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.CN1CCOCC1.P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl.CO.O>[NH2:10][C@@H:11]1[C:30](=[O:31])[N:13]2[C:14]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[C:15]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[CH2:16][S:17][C@H:12]12
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 54439270t-Butyl (6R,7R)-7-Phenylacetamido-3-[(RS)-tetra-hydrofuran-3-yl]ceph-3-em-4-carboxylate

生成物 1

HCID 54127982t-Butyl (6R,7R)-7-Amino-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

t-Butyl (6R,7R)-7-phenylacetamido-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate (0.9 g) in dichloromethane (15 ml) with N-methylmorpholine (0.45 g, 0.49 ml) was successively treated with phosphorus pentachloride (0.549 g) in dichloromethane (13.74 ml), methanol (10 ml) and water (10 ml) as described in Example 2(f). After purification by flash chromatography on silica gel eluting with 60, 80% ethyl acetate/hexane and then ethyl acetate, the title compound was obtained as a yellow solid (0.481 g, 73%); (Found: M+, 326.1304. C15H22N2O4S requires M, 326.1300); νmax (CH2Cl2) 3408, 1775 and 1716 cm-1 ; δH (CDCl3) 1.55 (9H, s), 1.69-2.41 (3H, m's), 3.31 and 3.48 with 3.34 and 3.49 (2H, 2ABq's, J 17.5 and 17.5 Hz), 3.69-3.83 (4H, 2s's overlapping m), 3.97-4.05 (2H, m), 4.72 and 4.74 (1H, 2d's, J 4.3 and 4.4 Hz) and 4.95 and 4.97 (1H, 2d's, J 4.3 and 4.4 Hz).

後処理

  1. customAfter purification by flash chromatography on silica gel eluting with 60, 80% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-a41943beccaa4832ba42e50fe3f04261
出典データセット
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06077952

反応ノート

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