Sodium Hydroxide → HCID 178444544, 화합물

HRID 1077954

반응식

HRID 1077954 반응식
[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]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 90624D-AllothreonineHCID 178444557HCID 178444557, 화합물

생성물 1

HCID 178444544HCID 178444544, 화합물

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

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% CH3OH and 0.4% HOAc in CH2Cl2): NMR δ 0.88 (t, J≈7, 3 H), 4.15 (m, 1 H), 4.54 (m, 1 H), 6.49 (d, 1H); MS (CI, CH4) m/z 300 (M+H).

후처리

  1. customExcess reagent is removed in vacuo
  2. customis purified by chromatography (1.5×18 cm column, 5% CH3OH and 0.4% HOAc in CH2Cl2)

출처 및 근거

ORD 기록
ord-de4f0d60357542b5b51915f581690b98
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05545662

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