Sodium Hydroxide → HCID 178444544、化合物

HRID 52247

反応式

HRID 52247 の反応式
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)(=O)C(Cl)=O.[NH2:21][C@@H:22]([C:26]([OH:28])=[O:27])[C@@H:23]([CH3:25])[OH:24].[OH-].[Na+]>C1(C)C=CC=CC=1.C(#N)C.C1COCC1>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]([NH:21][C@@H:22]([C:26]([OH:28])=[O:27])[C@@H:23]([CH3:25])[OH:24])=[O:14])[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 90624D-AllothreonineHCID 178444557HCID 178444557、化合物

生成物 1

HCID 178444544HCID 178444544、化合物

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of trans-4-pentylcyclohexane carboxylic acid (198 mg, 1.0 mmol) in dry toluene (1 mL) is treated with oxalyl chloride (760 mg, 5.9 mmol) at 0° C. and the mixture is stirred for 2 h at the same temperature and 1 h at room temperature. Excess reagent is removed in vacuo. A solution of the crude acid chloride in dry acetonitrile (2 mL) is added to a mixture of D-allo-Thr (100 mg, 0.85 mmol), 2N aq. NaOH (600 μl, 1.20 meq) and TEA (85 mg, 0.85 mmol) in THF (1.5 mL), following the procedure described in Example 1. The crude product 2c-6 is purified by chromatography (1.5×18 cm column, 5% CH2OH and 0.4% HOAc in CH2Cl2): NMR δ0.88 (t, J-7, 3H), 4.15 (m, 1H), 4.54 (m, 1H), 6.49 (d, 1H); MS (CI, CH4) m/z 300 (M+H).

後処理

  1. customExcess reagent is removed in vacuo
  2. customis purified by chromatography (1.5×18 cm column, 5% CH2OH and 0.4% HOAc in CH2Cl2)

出典と根拠

ORDレコード
ord-fbd312348060406281a4d40b92aaf98a
出典データセット
uspto-grants-1997_04
特許番号
US05616612

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