Sodium Methoxide → HCID 131723723, compound

HRID 2300963Notes

Reaction equation

HRID 2300963 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]=2)[CH2:11][C@H:10]1[S:31]C(=O)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:27]([O:26][C:24](=[O:25])[O:23][C:15]1[CH:14]=[CH:13][C:12]2[CH2:11][C@@H:10]([SH:31])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:17]=2[CH:16]=1)([CH3:29])([CH3:30])[CH3:28]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 88182850HCID 88182850, compound

Product 1

HCID 131723723HCID 131723723, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Thioacetic acid S-(trans-3-tert-butoxycarbonylamino-6-tert-butoxycarbonyloxy-4,4-diethyl-1,2,3,4-tetrahydro-naphthalen-2-yl) ester (234 mg, 0.47 mmol) in MeOH (5 mL) was added the sodium methoxide (54 μL, 0.95 mmol) and stirred at 0° C. for 30 min. The mixture was quenched with H2O, diluted with Et2O (50 mL), washed with H2O, HCl (10%), H2O, brine, dried over MgSO4. The residu was used without any other purification (151 mg, 71%). 1H NMR (CDCl3): 7.10-6.95 (3H, m, Har), 4.58 (1H, d, J=11.0 Hz, NH), 4.00 (1H, t, J=11 Hz, CHNH), 3.40-3.25 (2H, m), 2.98 (1H, m), 1.80-1.45 (22H, m), 0.80-0.70 (6H, m, CH3).

Workup

  1. customThe mixture was quenched with H2O
  2. additiondiluted with Et2O (50 mL)
  3. washwashed with H2O, HCl (10%), H2O, brine
  4. dry with materialdried over MgSO4
  5. customThe residu was used without any other purification (151 mg, 71%)

Sources & evidence

ORD record
ord-882fa6f08b23434abe081172b1f13f21
Source dataset
uspto-grants-2002_12
Patent number
US06498196B1

Reaction notes

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