Sodium Hydroxide → HCID 178444544, compound

HRID 1450736Notes

Reaction equation

HRID 1450736 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 178444544HCID 178444544, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 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).

Workup

  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)

Sources & evidence

ORD record
ord-1a57e3cdf7ba4b32b53f675e838cfe23
Source dataset
uspto-grants-1997_02
Patent number
US05602275

Reaction notes

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