Water → N-(Triphenylmethyl)-L-asparagine

HRID 1110188

반응식

HRID 1110188 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 15138256Z-Asn(trt)-OHHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 7408309N-(Triphenylmethyl)-L-asparagine

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 313Hydrochloric Acid용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-5842472ce65148f88bc63a31add77165
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324833

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