Dicyclohexylcarbodiimide → 8-{[(Benzyloxy)carbonyl]amino}-1,2,3,4-tetrahydronaphthalen-2-yl (2r)-methoxy(phenyl)acetate

HRID 1672542Notes

Reaction equation

HRID 1672542 reaction equation
[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[CH3:23][O:24][C@H:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26](O)=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:23][O:24][C@H:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26]([O:1][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[C:9]([NH:12][C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:22])[CH:8]=[CH:7][CH:6]=2)[CH2:11]1)=[O:27]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2724294(R)-(-)-alpha-methoxyphenylacetic acidHCID 66696602Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamate

Product 1

HCID 908939218-{[(Benzyloxy)carbonyl]amino}-1,2,3,4-tetrahydronaphthalen-2-yl (2r)-methoxy(phenyl)acetateYield 89.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of Example 24B (1.03 g, 3.46 mmol), (R)-2-methoxy-2-phenylacetic acid (0.633 g, 3.81 mmol), 1,3-dicyclohexylcarbodiimide (1.14 g, 5.54 mmol), and 4-dimethylaminopyridine (0.846 g, 6.93 mmol) in dichloromethane (35 mL) was stirred at ambient temperature for 18 hr. The reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NH4Cl solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was placed on a silica gel column and eluted with 30% ethyl acetate/hexanes to afford 1.38 g (89% yield) of the title compound as a colorless syrup. MS (ESI+) m/z 446 (M+H)+, 463 (M+NH4).

Workup

  1. washwashed with saturated aqueous NH4Cl solution, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washeluted with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-30bcf3f86cde46caadba104865280780
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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