Sodium Bicarbonate → (2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic Acid

HRID 463366ノート

反応式

HRID 463366 の反応式
C(=O)(O)[O-].[Na+].[N+](C1C=CC(C[O:14][C:15]([C@@H:17]2[N:21]3[C:22](=[O:35])[C@@H:23]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:20]3[S:19][C@:18]2([CH2:37][O:38][C:39](=[O:44])[NH:40][C:41](=[O:43])[CH3:42])[CH3:36])=[O:16])=CC=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[C:41]([NH:40][C:39]([O:38][CH2:37][C@@:18]1([CH3:36])[C@H:17]([C:15]([OH:16])=[O:14])[N:21]2[C:22](=[O:35])[C@@H:23]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:20]2[S:19]1)=[O:44])(=[O:43])[CH3:42]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 12817532(2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic acid p-nitrobenzyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 18598135(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic Acid収率 87%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 10% palladium on charcoal (400 mg) in ethyl acetate (40 ml) and aqueous 0.5% sodium bicarbonate was prehydrogenated and charged with (2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic acid p-nitrobenzyl ester (400 mg 0.68 mmol). The whole was shaken at 50 psi hydrogen pressure for 30 minutes and polish filtered. The aqueous was washed with ethyl acetate (20 ml), combined with a back extract of H2O (20 ml), overlayed with ethyl acetate (25 ml) and adjusted to pH 2.9 with 35% sulfuric acid. The layers were separated and the rich organic phase was washed with water (20 ml), combined with a back extract (EtOAc, 20 ml), dried (4A sieves), polish filtered and concentrated in vacuo to a colorless foam (270 mg) in 87% yield; nmr 100 MHz (CDCl3 --D2O) ppm 7.32 (2, m, m-phenyl H's) 6.96 (3, m, o,p-phenyl H's), 5.59 (2, br s, mag. equiv. C5,C6 --H's), 4.79 (1, s, C3 --H), 4.59 (HOD and ##STR65## 4.08 (m, AB of C2 --CH2O), 2.25 (3, s, ##STR66## and 1.58 (3, s, C3 --Me) with small ethyl acetate impurity.

後処理

  1. filtrationpolish filtered
  2. washThe aqueous was washed with ethyl acetate (20 ml)
  3. extractiona back extract of H2O (20 ml), overlayed with ethyl acetate (25 ml)
  4. customThe layers were separated
  5. washthe rich organic phase was washed with water (20 ml)
  6. extractionextract (EtOAc, 20 ml)
  7. dry with materialdried (4A sieves), polish
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a colorless foam (270 mg) in 87% yield

出典と根拠

ORDレコード
ord-f2486907407b470ca38d8533a6d6e62e
出典データセット
uspto-grants-1985_05
特許番号
US04518773

反応ノート

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