1,2-Dichloroethane → [[2-(Methoxymethylamino)-2-oxoethyl][(phenylmethoxy)carbonyl]amino]-acetic acid

HRID 2114847ノート

反応式

HRID 2114847 の反応式
[CH2:1]([O:8][C:9]([N:11]([CH2:16][C:17]([OH:19])=O)[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.Cl.[CH3:25][O:26][CH2:27][NH2:28].CCN(C(C)C)C(C)C.Cl>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:25][O:26][CH2:27][NH:28][C:17](=[O:19])[CH2:16][N:11]([CH2:12][C:13]([OH:15])=[O:14])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 10107013N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycineHCID 21959107Methoxymethanamine hydrochloride

生成物 1

HCID 69172672[[2-(Methoxymethylamino)-2-oxoethyl][(phenylmethoxy)carbonyl]amino]-acetic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To a solution of N-[(benzyloxy)carbonyl]-N-(carboxymethyl)glycine (28.45 g, 106.46 mmol) in DMF (163 mL) was added EDC (24.08 g, 125.62 mmol). The solution was cooled to 0° C. and treated with a mixture of N-methoxymethylamine hydrochloride (12.25 g, 125.62 mmol) and Hunig's base (21.88 mL, 125.62 mmol) in DMF (55 mL). The reaction was stirred at room temperature overnight and poured over a mixture of ice and aqueous 10% HCl solution. The mixture was extracted twice with EtOAc. The combined organics were washed twice with aqueous 10% HCl solution and once with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford a crude oil which was suspended in saturated aqueous NaHCO3 solution. The mixture was washed with EtOAc, adjusted to pH 2 with aqueous 1N HCl, and extracted three times with EtOAc. The final three organic extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to afford the product as a golden oil.

後処理

  1. extractionThe mixture was extracted twice with EtOAc
  2. washThe combined organics were washed twice with aqueous 10% HCl solution and once with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a crude oil which
  7. washThe mixture was washed with EtOAc
  8. extractionextracted three times with EtOAc
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5f9615fc4fea4aae9d6082b42316b8bc
出典データセット
uspto-grants-2008_10
特許番号
US07435735B2

反応ノート

読み込み中…