1,2-Dichloroethane → HCID 70154446, compound

HRID 1018665Notes

Reaction equation

HRID 1018665 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:15]2[CH:16]=[C:17]([C:28]([OH:30])=O)[C:18]([O:20][CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:19][C:14]=2[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:37]C=2C=1.C(Cl)CCl.[NH4+].[OH-]>C(Cl)Cl.CN(C=O)C.Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[C:15]2[CH:16]=[C:17]([C:28](=[O:30])[NH2:37])[C:18]([O:20][CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:19][C:14]=2[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 10693291HCID 10693291, compound

Product 1

HCID 70154446HCID 70154446, compoundYield 333.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To 9-tert-butoxycarbonylamino-3-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid (1.5 g, 3.60 mmol) in CH2Cl2/DMF (4:1, 25 mL) was added HOBT (0.53 g, 4.0 mmol) and EDC (0.76 g, 4.0 mmol) and the mixture allowed to stir for 30 min. To this was added NH4OH (27% aqueous, 0.30 mL, 4.0 mmol) and stirring was continued for 3 h. The mixture was diluted with 1 M HCl and extracted with EtOAc. The combined extracts were washed with water, sat'd NaHCO3, dried over magnesium sulfate,and concentrated to a solid. The solid was recrystallized from Et2O to yield a white solid (5.0 g, 68%). MS [M−H]− 415, m.p. 193-194° C.

Workup

  1. stirringstirring
  2. waitwas continued for 3 h
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate,and
  6. concentrationconcentrated to a solid
  7. customThe solid was recrystallized from Et2O

Sources & evidence

ORD record
ord-6a47b00493954ed48558ea68c7a4212e
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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