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4-Methylmorpholine → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

HRID 1462114
ノート
印刷プレビュー

反応式

HRID 1462114 の反応式
C([CH2:8][C@H:9]([NH2:13])[C:10]([OH:12])=[O:11])C[C@@H](N)C(O)=O.NC[C:16]([OH:18])=[O:17].CN1CC[O:23][CH2:22][CH2:21]1.[CH2:26](OC(Cl)=O)[CH:27]([CH3:29])[CH3:28].C[Si]([CH:38]([Si](C)(C)C)[C:39]([NH2:41])=[O:40])(C)C>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[NH:13]([C:16]([O:18][C:27]([CH3:26])([CH3:28])[CH3:29])=[O:17])[C@@H:9]([C:10]([O:12][N:41]1[C:22](=[O:23])[CH2:21][CH2:38][C:39]1=[O:40])=[O:11])[CH3:8]
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

8

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11708267BistrimethylsilylacetamidHCID 87968512meso-DAP (D)GlyOH

生成物 1

HCID 11580086N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-10 °C

実験手順

D-Lac(oAc)-L-Phe-D-GluoBzl (2) (1.0 g) was dissolved in methylene chloride (40 ml) and N-methylmorpholine (200 mg) was added thereto. To this stirred solution cooled at -10° C. in an ice salt-bath, isobutylchlorocarbonate (270 mg) was added and the mixture was allowed to react at the same temperature for 20 minutes. To the reaction mixture was added the silyl ester prepared from Boc-(D)-mesoDAP-(D)-NHNHBoc-(L)-GlyOH (1) (920 mg) in a mixture of methylene chloride (20 ml) and dimethylformamide (10 ml) containing bis(trimethylsilyl)acetamide (2 ml). The reaction mixture was stirred for 2 hours and concentrated under reduced pressure to give an oily residue which was dissolved in ethyl acetate and washed with 2% hydrochloric acid. The organic layer was washed successively with water and saturated sodium chloride and then dried. Evaporation of the solvent gave a residue which was throughly washed with ether and collected by filtration to give D-Lac(oAc)-L-Phe-γ-D-Glu(α-oBzl)-(L)-Boc-(D)-mesoDAP-(D)-NHNHBoc-(L)-GlyOH (3) (1.660 g).

後処理

  1. customto react at the same temperature for 20 minutes
  2. concentrationconcentrated under reduced pressure
  3. customto give an oily residue which
  4. washwashed with 2% hydrochloric acid
  5. washThe organic layer was washed successively with water and saturated sodium chloride
  6. customdried
  7. customEvaporation of the solvent
  8. customgave a residue which
  9. washwas throughly washed with ether
  10. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-cb26e0b02ad344d7918596c4f3578377
出典データセット
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04458078

反応ノート

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