Hydrochloric Acid → HCID 54559825、化合物

HRID 366097ノート

反応式

HRID 366097 の反応式
[OH-].[Na+].Cl.[C:4]([NH:14][CH2:15][CH2:16][CH2:17][C@H:18]([C:20]([OH:22])=[O:21])[NH2:19])([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:23]1([CH:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C1COCC1>[C:4]([NH:14][CH2:15][CH2:16][CH2:17][C@H:18]([C:20]([OH:22])=[O:21])[NH:19][C:30](=[O:31])[CH:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 746372,2-Diphenylacetyl chlorideHCID 69885572(2R)-2-amino-5-[(benzyloxy)carbonyl]aminopentanoic acid hydrochloride

生成物 1

HCID 54559825HCID 54559825、化合物収率 91.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1 N NaOH (75 mL) was added to a stirred suspension of (R)-N5 -(Cbz)-ornithine hydrochloride (7.5 g; 25 mmol) in THF (114 mL). Once the starting material had dissolved, diphenylacetyl chloride (6.7 g; 26.3 mmol) was added. The reaction was stirred for 3 h at room temperature, then made acidic with cold 1 N HCl and extracted with EtOAc (3×75 mL). The EtOAc extract was washed with brine, dried with Na2SO4, and concentrated to afford the crude product. Purification by flash chromatography on silica eluting with EtOAc:hexanes (1:1) afforded the sub-title compound (10.5 g; 91%).

後処理

  1. dissolutionOnce the starting material had dissolved
  2. extractionextracted with EtOAc (3×75 mL)
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by flash chromatography on silica eluting with EtOAc:hexanes (1:1)

出典と根拠

ORDレコード
ord-17a7b31f36c146a3a93a681869d39f9a
出典データセット
uspto-grants-2000_10
特許番号
US06127414

反応ノート

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