Hydrochloric Acid → N-[(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3 hydroxypropionyl]-L-tryptophan benzyl ester

HRID 1533279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533279
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH:16]([CH:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[OH:21])[C:17](O)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:29]([O:36][C:37](=[O:50])[C@H:38]([CH2:40][C:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[NH:43][CH:42]=1)[NH2:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.CN1CCOCC1.Cl>CN(C)C=O.C(OCC)C>[CH2:29]([O:36][C:37](=[O:50])[C@H:38]([CH2:40][C:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[NH:43][CH:42]=1)[NH:39][C:17](=[O:18])[CH:16]([CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:20]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[OH:21])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22012301(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionic acidHCID 45073232L-tryptophan benzyl ester hydrochloride

Produkt 1

HCID 70244716N-[(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3 hydroxypropionyl]-L-tryptophan benzyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionic acid (111 mg) in dimethylformamide (3 ml) were added L-tryptophan benzyl ester hydrochloride (198 mg), 1-hydroxybenzotriazole hydrate (60.8 mg), 1,3-dicyclohexylcarbodiimide (80.5 mg) and 4-methylmorpholine (91 mg) successively. After being stirred for 16 hours at ambient temperature, the mixture was poured into a mixture of diethyl ether and aqueous 1N hydrochloric acid solution. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layer was washed with aqueous bicarbonate solution and brine, dried and evaporated under reduced pressure. The residue was purified by chromatography to afford N-[(2RS,3RS)-2-(2-benzyloxyphenylmethyl)-3-cyclohexyl-3 hydroxypropionyl]-L-tryptophan benzyl ester (171 mg).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. washThe combined organic layer was washed with aqueous bicarbonate solution and brine
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9e07714625664cb39419a8e863134df5
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207686B1

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