Triethylamine → (2R,4S)-2-benzyl-1-(3,5-bis(trifluoromethyl)benzoyl)-N-(2-phenylethyl)-N-trifluoroacetyl-4-piperidinamine

反応式

[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:45])([F:44])[C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[C:34](O)=[O:35].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C>>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10][N:9]1[C:34](=[O:35])[C:33]1[CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=[C:31]([C:30]([F:29])([F:44])[F:45])[CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

反応物 4

HCID 8471Triethylamine

HCID 128893,5-Bis(trifluoromethyl)benzoic acid

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

HCID 22863105(2R*,4S*)-2-Benzyl-N-(2-phenylethyl)-N-trifluoroacetyl-4-piperidinamine

生成物 1

HCID 57308278(2R*,4S*)-2-benzyl-1-(3,5-bis(trifluoromethyl)benzoyl)-N-(2-phenylethyl)-N-trifluoroacetyl-4-piperidinamine収率 79%

実験手順

150 mg (0.384 mmol) of (2R*,4S*)-2-benzyl-N-(2-phenylethyl)-N-trifluoroacetyl-4-piperidinamine are reacted in analogy to Example 4a with 93 mg (0.461 mmol) of 3,5-bis(trifluoromethyl)benzoic acid, 117 mg (0.461 mmol) of bis(2-oxo-3-oxazolidinyl)phosphinic chloride and 118 μl (0.845 mmol) of triethylamine. The title compound (191 mg, 79%) is obtained as oil. TLC:methylene chloride/methanol/cone. ammonia (2000:50:1) Rf =0.79, FD-MS:M+ =630.

出典と根拠

ORDレコード: ord-bd6599b3ddd64548b11a3cd00edf8d56
出典データセット: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05646144

反応ノート

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