1,2-Dichloroethane → HCID 178445685, compound

HRID 1992792Notes

Reaction equation

HRID 1992792 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[N:17]=[C:16]([C:29]3[CH:34]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C([O:61][C:62](=[O:66])[CH2:63][CH2:64][NH2:65])(C)(C)C.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:65][CH2:64][CH2:63][C:62]([OH:61])=[O:66])=[O:25])=[CH:22][CH:21]=3)[N:17]=[C:16]([C:29]3[CH:30]=[C:31]([F:37])[C:32]([F:36])=[C:33]([F:35])[CH:34]=3)[CH:15]=2)=[O:13])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 4192171tert-Butyl 3-aminopropanoateHCID 178445686HCID 178445686, compound

Product 1

HCID 178445685HCID 178445685, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the intermediate from example 1 step F (90 mg, 0.175 mmol) in DMF was added HOAt (36 mg, 0.26 mmol), DIEA (92 μL, 0.52 mmol), β-alanine-tert-butyl ester(48 mg, 0.26 mmol) and EDC (50 mg, 0.26 mmol). After stirring the reaction at room temperature for 18 hours it was diluted with ethyl acetate (20 mL), washed with 1N HCl, saturated NaHCO3, and saturated NaCl. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified on the Biotage quad 3 using 30% ethyl acetate-hexanes to give the title compound. 1H NMR (CDCl3, 500 MHz): 7.72 (d, J=8.3 Hz, 2H), 7.45 (t, J=6.9 Hz, 2H), 7.40 (d, J=8.2 Hz, 2H), 6.87 (bt, J=5.5 Hz, 1H), 6.73 (s, 1H), 5.83 (s, 2H), 3.9 (m, 1H), 3.7 (q, J=6.0 Hz, 2H), 2.57 (t, J=6.0 Hz, 2H), 2.1 (bm, 2H), 1.9 (bm, 2H), 1.47 (s, 9H), 1.2-1.4 (m, 4H), 0.88 (s, 9H). LC-MS: 4.55 min; (M+H)=641.5.

Workup

  1. customthe reaction at room temperature for 18 hours it
  2. washwashed with 1N HCl, saturated NaHCO3, and saturated NaCl
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on the Biotage quad 3 using 30% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-79c0a0d39e294156ada2271cfaadd67d
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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