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Hydrochloric Acid → N-[2-[(1-Pyrrolidinylcarbonyl)amino]-5-(trifluoromethyl)benzoyl]glycine

HRID 1825035
ノート
印刷プレビュー

反応式

HRID 1825035 の反応式
[N:1]1([C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:10]=2C(O)=O)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCCC1.CN1CC[O:31][CH2:30]C1.Cl.C([O:42][C:43](=[O:46])[CH2:44][NH2:45])C1C=CC=CC=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C.CCOC(C)=O>[N:1]1([C:6]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:10]=2[C:30]([NH:45][CH2:44][C:43]([OH:42])=[O:46])=[O:31])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 221431222-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic acid

生成物 1

HCID 21991137
N-[2-[(1-Pyrrolidinylcarbonyl)amino]-5-(trifluoromethyl)benzoyl]glycine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

2-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic acid (made analogously to Example 116 with pyrrolidine in place of iso-butylamine (2.9 g) was dissolved in DMF (40 mL). After cooling to 0° C., 4-methylmorpholine (3.2 mL) and glycine benzyl ester hydrogen chloride (5.6 g) were added. After 5 min, BOP Reagent (5.6 g) was added and the mixture was stirred at rt for 18 h. EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl, NaHCO3 solution, and brine. The EtOAc was dried (MgSO4), filtered, and concentrated to a solid (2.6 g). This solid was dissolved in MeOH (14 mL) prior to the addition of 10% Pd/C. A hydrogen balloon was added and the solution was stirred for 1 h. The palladium was filtered and the solution was concentrated to give the title glycine derivative (2.0 g) as a white solid. MS found: (M+H)+=360.2.

後処理

  1. washThe EtOAc layer was washed with 1 N HCl, NaHCO3 solution, and brine
  2. dry with materialThe EtOAc was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to a solid (2.6 g)
  5. dissolutionThis solid was dissolved in MeOH (14 mL)
  6. additionto the addition of 10% Pd/C
  7. additionA hydrogen balloon was added
  8. stirringthe solution was stirred for 1 h
  9. filtrationThe palladium was filtered
  10. concentrationthe solution was concentrated

出典と根拠

ORDレコード
ord-f8b5c851fa7a472e8a227d2a9051841f
出典データセット
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07045521B2

反応ノート

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