Hydrochloric Acid → N-[(1S)-3-hydroxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide hydrochloride

HRID 1964810노트

반응식

HRID 1964810 반응식
[OH:1][CH2:2][CH2:3][C@H:4]([NH:11][C:12]([CH:14]1[N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16][S:15]1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:26]>C(Cl)Cl.O1CCOCC1>[ClH:26].[OH:1][CH2:2][CH2:3][C@H:4]([NH:11][C:12]([CH:14]1[NH:18][CH2:17][CH2:16][S:15]1)=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 60036810tert-butyl 2-({[(1S)-3-hydroxy-1-phenylpropyl]amino}carbonyl)-1,3-thiazolidine-3-carboxylate

생성물 1

HCID 68623384N-[(1S)-3-hydroxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide hydrochloride

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

A solution was made containing a compound of general structure (V) (Intermediate 6, 0.788 g, 2.15 mmol), e.g., tert-butyl 2-({[(1S)-3-hydroxy-1-phenylpropyl]amino}carbonyl)-1,3-thiazolidine-3-carboxylate, in anhydrous DCM (50 ml). At 0° C., 4M HCl solution in dioxane (50 ml) was added, or alternatively, HCl gas, previously dried with a H2SO4 cc trap, was bubbled slowly through the reaction and deprotection was monitored by TLC using cyclohexane/ethyl acetate (1/1) and stained with a pancaldi solution. After approximately 45 minutes, TLC showed no remaining starting materiel and DCM was then evaporated in vacuo without heating to avoid salt decomposition. More DCM (20 ml) was then added and evaporated again in vacuo to remove remaining potential HCl (2-3 times). The desired product, e.g., N-[(1S)-3-hydroxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide hydrochloride, was isolated as a white solid and used for the next step without further purification and characterization.

후처리

  1. dry with materialalternatively, HCl gas, previously dried with a H2SO4 cc trap
  2. customwas bubbled slowly through the reaction and deprotection
  3. customwas then evaporated in vacuo
  4. temperaturewithout heating
  5. additionMore DCM (20 ml) was then added
  6. customevaporated again in vacuo
  7. customto remove

출처 및 근거

ORD 기록
ord-8c29e7b633e047868b2ce578144512ce
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415480B2

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