Water → N-(Triphenylmethyl)-L-asparagine

HRID 1110188

反応式

HRID 1110188 の反応式
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H][H].C(N(CC)CC)C.O>Cl.[Pd]>[NH2:1][C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 15138256Z-Asn(trt)-OHHCID 178418361HCID 178418361、化合物

生成物 1

HCID 7408309N-(Triphenylmethyl)-L-asparagine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 313Hydrochloric Acid溶媒

実験手順

A suspension of 10.2 g of Z-Asn(Trt)-OH (20 mmol) in 120 ml of one-normal aqueous hydrochloric acid is hydrogenated in the presence of 0.5 g of a 10% palladium on charcoal catalyst at room temperature and under atmospheric pressure. After uptake of hydrogen is complete, the catalyst is filtered off and thoroughly washed with methanol, and the filtrate is concentrated under reduced pressure to a weight of 100 g. Addition of 2.8 ml of triethylamine (20 mmol) is followed by further concentration to a weight of 50 g and the crystalline precipitate is filtered off and washed with a 1:1 mixture of methanol and water and then with water until free of chloride. The H-Asn(Trt)-OH contains 0.5 mole of water and slowly decomposes above 220°.

後処理

  1. filtrationthe catalyst is filtered off
  2. washthoroughly washed with methanol
  3. concentrationthe filtrate is concentrated under reduced pressure to a weight of 100 g
  4. concentrationis followed by further concentration to a weight of 50 g
  5. filtrationthe crystalline precipitate is filtered off
  6. washwashed with a 1:1 mixture of methanol and water

出典と根拠

ORDレコード
ord-5842472ce65148f88bc63a31add77165
出典データセット
uspto-grants-1994_06
特許番号
US05324833

関連ノート

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