1,2-Dichloroethane → HCID 19034123, compound

HRID 265870Notes

Reaction equation

HRID 265870 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[C:17](CCC(O)=O)[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C[C:29]2N(O)N=N[C:30]=2[CH:31]=1.N(CC)(C(C)C)[CH:37](C)C.Cl.C(NC[CH2:52][C:53]([OH:55])=[O:54])(C)(C)C.[CH2:56](Cl)[CH2:57]Cl.[CH3:60][N:61]([CH:63]=[O:64])C>>[C:30]([O:55][C:53](=[O:54])[CH2:52][CH2:60][NH:61][C:63](=[O:64])[CH2:56][CH2:57][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)[CH:16]=1)([CH3:29])([CH3:31])[CH3:37]

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 17567357N-tert-Butyl-beta-alanine--hydrogen chloride (1/1)HCID 19034073HCID 19034073, compound

Product 1

HCID 19034123HCID 19034123, compound

Procedure

To a stirred solution of 11-7 (275 mg, 0.79 mmoles), HOBT (130 mg, 0.95 mmoles), N(i-Pr)2Et (0.55 mL, 3.2 mmoles), tert-butyl-β-alanine hydrochloride (160 mg, 0.95 mmoles), and DMF (4 mL), at -15° C. was added EDC (183 mg, 0.95 mmoles) followed by removal of the cooling bath. After 20 hours the reaction mixture was diluted with EtOAc and then washed with H2O, saturated NaHCO3, 10% KHSO4, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 50% EtOAc/hexanes) gave 11-8 as a colorless oil. Rf 0.21 (silica, 50% EtOAc/hexanes).

Workup

  1. customfollowed by removal of the cooling bath
  2. additionAfter 20 hours the reaction mixture was diluted with EtOAc
  3. washwashed with H2O, saturated NaHCO3, 10% KHSO4, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b417981ff1b436c9e32fb68a6d9479c
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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