1,2-Dichloroethane → (R)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 2201045ノート

反応式

HRID 2201045 の反応式
[C:1]([NH:11][C@@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1C=C2[N:29]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:29][C:20](=[O:22])[C@H:12]([NH:11][C:1](=[O:2])[O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 68077307(R)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate収率 91.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-Cbz-D-phenylalanine (1.00 g, 3.34 mmol) and HOBt hydrate (0.614 g, 4.01 mmol) in DMF (9 mL), EDC (0.834 g, 4.34 mmol) was added. The mixture was stirred for 40 min. Then conc. NH4OH (1.00 mL, ˜14 mmol) was added. It was stirred for 72 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-benzyl 1-amino-1-oxo-3-phenylpropan-2-ylcarbamate as a solid (0.910 g).

後処理

  1. stirringIt was stirred for 72 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4d2e2998707c488986807568655e45c3
出典データセット
uspto-grants-2016_06
特許番号
US09359375B2

反応ノート

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