1-Hydroxybenzotriazole → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

HRID 342625

反応式

HRID 342625 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][O:23][CH3:24].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH3:24][O:23][N:22]([CH3:21])[C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

実験手順

2(S)-(tert-Butoxycarbonylamino)-3-phenylpropionic acid (39.80 g, 0.150 mol), N,O-dimethylhydroxylamine hydrochloride (21.95 g, 0.225 mol), EDC hydrochloride (31.52 g, 0.165 mol) and HOBT (20.25 g, 0.150 mol) were stirred in dry, degassed DMF (200 mL) at 20° C. under nitrogen. N-Methylmorpholine is added to obtain pH 7. The reaction was stirred overnight, the DMF distilled under high vacuum, and the residue partitioned between ethyl acetate and 2% potassium hydrogen sulfate. The organic phase was washed with saturated sodium bicarbonate, water, and saturated brine, and dried with magnesium sulfate. The solvent was removed in vacuo to give the title compound.

後処理

  1. customin dry
  2. customdegassed DMF (200 mL) at 20° C. under nitrogen
  3. additionN-Methylmorpholine is added
  4. customto obtain pH 7
  5. distillationthe DMF distilled under high vacuum
  6. customthe residue partitioned between ethyl acetate and 2% potassium hydrogen sulfate
  7. washThe organic phase was washed with saturated sodium bicarbonate, water, and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-ae2da7e1994e4270bf1f4ba7da5da323
出典データセット
uspto-grants-1999_01
特許番号
US05859012

関連ノート

読み込み中…