Ethyl Acetate → HCID 12393690, compound

HRID 259012Notes

Reaction equation

HRID 259012 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[C:12]([O:14][CH3:15])=[O:13])[C@H:3]1[OH:24].[C:25]([O:28][CH2:29][CH3:30])(=[O:27])C.C(Cl)(=O)OCC.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:17]([O:16][C:7]1[C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:9]2[C:4](=[CH:5][CH:6]=1)[C@@H:3]([OH:24])[C@H:2]([NH:1][C:25]([O:28][CH2:29][CH3:30])=[O:27])[CH2:11][CH2:10]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 12393665HCID 12393665, compound

Product 1

HCID 12393690HCID 12393690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.0 g. of trans-2-amino-6-benzyloxy-1-hydroxy-5-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene in 20 ml. of ethyl acetate are added 5 ml. of water and 400 mg. of ethyl chlorcarbonate, and with stirring at room temperature, 1.0 g. of anhydrous potassium carbonate is added in small portions. After one-hour stirring, the organic layer is recovered, washed with water, dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate-n-hexane to obtain trans-6-benzyloxy-2-ethoxycarbonylamino-1-hydroxy-5-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene as colorless needles melting at 147°-148° C.

Workup

  1. customthe organic layer is recovered
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-70108a1c59bf4136837270baf3a6ebad
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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