1,2-Dichloroethane → HCID 67333112, compound

HRID 1669647Notes

Reaction equation

HRID 1669647 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)[CH2:13][CH2:12][CH:11]([C:14]([F:17])([F:16])[F:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH2:28]([O:30][C:31](=[O:35])[CH2:32][CH2:33][NH2:34])[CH3:29].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH:34][CH2:33][CH2:32][C:31]([O:30][CH2:28][CH3:29])=[O:35])=[O:23])=[CH:25][CH:26]=3)[CH2:13][CH2:12][CH:11]([C:14]([F:15])([F:16])[F:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 67333584HCID 67333584, compound

Product 1

HCID 67333112HCID 67333112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the title compound of Example 4, Step A (43 mg, 0.09 mmol), β-alanine ethyl ester hydrochloride (28 mg, 0.18 mmol), HOBt (28 mg, 0.18 mmol) and EDC (35 mg, 0.18 mmol) in 1 mL of DMF was added DIEA (0.047 mL, 0.27 mmol). The reaction was heated at 50° C. for 1.5 h, then partitioned between EtOAc/brine. The organic layer was collected and the aqueous layer was washed twice with EtOAc. The combined organic phase was concentrated under reduced pressure to provide the title compound. LC-MS (ESI): m/z=464.3 [M+1]+.

Workup

  1. custompartitioned between EtOAc/brine
  2. customThe organic layer was collected
  3. washthe aqueous layer was washed twice with EtOAc
  4. concentrationThe combined organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-43606eab24234cca803df0cf8ebfab62
Source dataset
uspto-grants-2011_08
Patent number
US07989472B2

Reaction notes

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