Diisopropylethylamine → (S)-5-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 2168772ノート

反応式

HRID 2168772 の反応式
[CH2:1]([C:5]1[N:10]=[N:9][C:8]([C:11]([OH:13])=O)=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:51]([O:55][C:56]([N:58]1[CH2:62][C@H:61]([CH2:63][NH2:64])[O:60][C:59]1([CH3:66])[CH3:65])=[O:57])([CH3:54])([CH3:53])[CH3:52].CCN(C(C)C)C(C)C>CN(C=O)C.CCOCC.O>[C:51]([O:55][C:56]([N:58]1[CH2:62][C@H:61]([CH2:63][NH:64][C:11]([C:8]2[N:9]=[N:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:6]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:18][CH:19]=3)[CH:7]=2)=[O:13])[O:60][C:59]1([CH3:66])[CH3:65])=[O:57])([CH3:54])([CH3:53])[CH3:52]

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673720716-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acidHCID 67373621(S)-5-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 67373730(S)-5-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (Example 93, 0.34 mmol, 0.12 g), HBTU (0.34 mmol, 0.13 g) and (S)-5-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.34 mmol, 0.05 mL) in DMF was added DIEA (1.0 mmol, 0.17 mL). Upon completion of the reaction, the mixture was diluted with ether, and then poured into water. The resulting mixture was extracted, the organic layer was dried. The solvent was removed, and the resulting residue was chromatographed with 4:1 hexane/EtOAc to provide (S)-5-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester was used as is in the next step. LCMS: m/z 566.9 [M+1].

後処理

  1. customUpon completion of the reaction
  2. extractionThe resulting mixture was extracted
  3. customthe organic layer was dried
  4. customThe solvent was removed
  5. customthe resulting residue was chromatographed with 4:1 hexane/EtOAc

出典と根拠

ORDレコード
ord-33ab46cd4abf44e389ac43b4a0f46da9
出典データセット
uspto-grants-2015_06
特許番号
US09045461B2

反応ノート

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