1,2-Dichloroethane → Acetic acid 3-{2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-4-oxo-azetidin-2-yl ester

HRID 460418Notes

Reaction equation

HRID 460418 reaction equation
[N:1]1([C:7]([NH:9][CH:10]([CH2:14][S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C:11]([OH:13])=O)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:25][CH:26]1[C:29](=[O:30])[NH:28][CH:27]1[O:31][C:32](=[O:34])[CH3:33].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>ClCCl>[N:1]1([C:7]([NH:9][CH:10]([CH2:14][S:15]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:16])=[O:17])[C:11]([NH:25][CH:26]2[C:29](=[O:30])[NH:28][CH:27]2[O:31][C:32](=[O:34])[CH3:33])=[O:13])=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 112797342-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acidHCID 19350682Acetic acid 3-amino-4-oxo-azetidin-2-yl ester

Product 1

HCID 69443596Acetic acid 3-{2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-4-oxo-azetidin-2-yl esterYield 12.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (100 mg, 0.28 mmol), acetic acid 3-amino-4-oxo-azetidin-2-yl ester (52 mg, 0.36 mmol), EDC (100 mg, 0.52 mmol), and HOBt (100 mg, 0.64 mmol) were combined. Dichloromethane (2 mL) was added and then 4-methylmorpholine (0.2 mL). The mixture was stirred at ambient temperature for 2 h. After dilution with ethyl acetate (100 mL) the solution was washed with 1N aqu. HCl (30 mL), sat. aqu. NaHCO3 (30 mL) and brine (30 mL), dried with MgSO4 and evaporated under vacuum. The residue was subjected to flash chromatography on silica gel (ethyl acetate) to give acetic acid 3-{2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionylamino}-4-oxo-azetidin-2-yl ester (17 mg, 0.035 mmol). 1H NMR: (DMSO) 9.18 (s, 1H), 8.72 (d, J=6.4 Hz, 1H), 7.41–7.30 (m, 5H), 7.08 (m, 1H), 5.76 (s, 1H), 4.80–4.61 (m, 2H), 4.49 (s, 2H), 3.63–3.22 (m, 10H), 2.08 (s, 3H). MS: (M+H)+ 483.

Workup

  1. washAfter dilution with ethyl acetate (100 mL) the solution was washed with 1N aqu
  2. dry with materialNaHCO3 (30 mL) and brine (30 mL), dried with MgSO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-d7a830e0fdb049f599782497f41520de
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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