Triethylamine → HCID 59547743, compound

HRID 2177082Notes

Reaction equation

HRID 2177082 reaction equation
C([O:5][C:6](=[O:27])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:18])=[CH:13][CH:14]=2)[CH:9]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)(C)(C)C.C(OC(=O)N[CH:35]1[CH2:44][CH2:43][C:42]2[C:37](=CC(O)=CC=2)[CH:36]1[CH2:46]C1C=CC(Cl)=C(Cl)C=1)(C)(C)C.C(N(CC)CC)C.C(Cl)(=O)OCC1C=CC=CC=1>CN(C)C=O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH:9]2[C:10]3[C:15](=[CH:14][CH:13]=[C:12]([OH:18])[CH:11]=3)[CH2:16][CH2:17][CH:8]2[NH:7][C:6](=[O:27])[O:5][CH2:46][C:36]2[CH:37]=[CH:42][CH:43]=[CH:44][CH:35]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 57467203HCID 57467203, compoundHCID 59547800HCID 59547800, compound

Product 1

HCID 59547743HCID 59547743, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl[1-(4-chlorobenzyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (2 g, 6.95 mmol, prepared analogously to tert-butyl[1-(3,4-dichlorobenzyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate, cf. example 34.2 were suspended in dimethylformamide (40 mL). Triethylamine (0.969 mL, 6.95 mmol) and benzyl carbonochloridate (1.186 g, 6.95 mmol) were added. The reaction mixture was stirred at room temperature over night. The solvent was evaporated in vacuo. To the crude product ethyl acetate and water were added. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 393 mg (0.931 mmol, 13.4%, colorless foam).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionTo the crude product ethyl acetate and water were added
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record
ord-b25d5ca3160241bb9b281486bf49cbbd
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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