Hydrochloric Acid → HCID 59284760、化合物

HRID 68222ノート

反応式

HRID 68222 の反応式
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]

参加物

10

反応物 4

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

生成物 1

HCID 59284760HCID 59284760、化合物収率 87.1%

試薬・触媒・溶媒 5

HCID 142844-(Dimethylamino)pyridine触媒HCID 3776Isopropanol溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-97ba62143bb649a1a1a136b4f913907e
出典データセット
uspto-grants-2014_09
特許番号
US08822424B2

反応ノート

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