1,2-Dichloroethane → HCID 15850750, compound

HRID 583668Notes

Reaction equation

HRID 583668 reaction equation
[C:1]([NH:11][CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[NH2:26][CH2:27][C@H:28]([NH:36][S:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:39])=[O:38])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[C:32]([O:31][C:29](=[O:30])[C@@H:28]([NH:36][S:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:39])=[O:38])[CH2:27][NH:26][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])=[CH:24][CH:23]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 15850760HCID 15850760, compoundHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Product 1

HCID 15850750HCID 15850750, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acid 15-3 (300 mg, 0.91 mmol), amine 2-1 (325 mg, 0.91 mmol), EDC (209 mg, 1.09 mmol), HOBT (148 mg, 1.10 mmol), and NMM (300 μL, 2.7 mmol) were combined in 4.5 mL DMF. After 16 h the mixture was diluted with EtOAc, washed with water, 10% KHSO4, sat NaHCO3, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 70% EtOAc/hexane) provided 15-4 as an off-white solid.

Workup

  1. washwashed with water, 10% KHSO4
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1ca47b68f8b94b08b63f50c551e20840
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

Loading…