Ammonia → (S)-4-Amino-N-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216986ノート

反応式

HRID 216986 の反応式
[C:1]([C@@H:3]([NH:21][C:22]([C:24]1([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[NH:16][C:15]=3[CH:20]=2)=[CH:7][CH:6]=1)#[N:2].N>C(O)=O.O>[NH2:30][C:24]1([C:22]([NH:21][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:18][C:17](=[O:19])[NH:16][C:15]=4[CH:20]=3)=[CH:9][CH:10]=2)=[O:23])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

参加物

5

反応物 2

HCID 222AmmoniaHCID 59568584(S)-tert-Butyl 4-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 59568558(S)-4-Amino-N-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 962Water溶媒

実験手順

(S)-tert-Butyl 4-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 33, step (ii), 160 mg) was heated at 50° C. in formic acid (0.5 mL) for 10 min. The cooled solution was diluted with water (50 mL) and basified with ‘880’ ammonia and the resulting precipitate extracted into ethyl acetate (200 mL). The dried extract was concentrated to dryness and purified purified by reversed phase HPLC (using a SunFire column) eluting with methanol/0.1% aqueous trifluoroacetic acid. The pure fractions were freeze dried to afford the titled compound as a trifluoroacetatic acid salt (36 mg) TFA salt as a colourless solid.

後処理

  1. extractionthe resulting precipitate extracted into ethyl acetate (200 mL)
  2. extractionThe dried extract
  3. concentrationwas concentrated to dryness
  4. custompurified
  5. custompurified by reversed phase HPLC (
  6. washeluting with methanol/0.1% aqueous trifluoroacetic acid
  7. customdried

出典と根拠

ORDレコード
ord-38eb457326b84c719fa57a4cba17d14b
出典データセット
uspto-grants-2012_06
特許番号
US08193239B2

反応ノート

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