Hydrochloric Acid → HCID 59284760, 화합물

HRID 241789노트

반응식

HRID 241789 반응식
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:7]([OH:18])[CH2:6]1)=[O:4].N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(O)(C)C.[OH-].[Na+].C(Cl)(Cl)Cl>[C:11]([NH:10][C@@H:8]1[CH2:9][C@H:5]([C:3]([OH:2])=[O:4])[CH2:6][C@@H:7]1[O:18][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

참가 물질

10

반응물 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734526methyl (1S,3R,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate

생성물 1

HCID 59284760HCID 59284760, 화합물수율 87.1%

시약·촉매·용매 5

HCID 142844-(Dimethylamino)pyridine촉매HCID 3776Isopropanol용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

To a stirring solution of N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester (0.622 g, 2.40 mmol) in DCM (1.9 mL) was added imidazole (0.164 g, 2.41 mmol), DMAP (0.047 g, 0.35 mmol) and TBSCl (0.363 g, 2.40 mmol) and the reaction was stirred at room temperature for 18 hours, followed by heating at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, and was quenched with H2O (3 mL). The organic layer was separated and was concentrated to dryness to yield a residue, which was dissolved in isopropanol (6 mL) and 1M NaOH (2.9 mL), and the reaction was heated at 60° C. for 1 hour. The reaction was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl (3 mL). After adding chloroform (18 mL), the organic layer was separated, dried over Na2SO4, and concentrated to dryness to yield the desired acid (0.75 g, 2.09 mmol, 87.1% yield).

후처리

  1. temperatureby heating at 40° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customwas quenched with H2O (3 mL)
  4. customThe organic layer was separated
  5. concentrationwas concentrated to dryness
  6. customto yield a residue, which
  7. temperatureThe reaction was cooled to 0° C.
  8. customthe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-89cd6993b5f8470380e7451a126626af
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653042B2

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