Hydrochloric Acid → HCID 46945559, compound

HRID 2370600Notes

Reaction equation

Cl.[CH3:2][C:3]1([CH3:49])[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([NH:19]C(=O)OC(C)(C)C)(=[O:18])=[O:17])=[C:11]([CH3:27])[CH:10]=2)[C:5](=[O:28])[N:4]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][S:38][CH2:39][CH2:40][CH2:41][C:42]([F:48])([F:47])[C:43]([F:46])([F:45])[F:44].C(Cl)Cl.CCOC(C)=O>C(OCC)C>[CH3:2][C:3]1([CH3:49])[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([NH2:19])(=[O:18])=[O:17])=[C:11]([CH3:27])[CH:10]=2)[C:5](=[O:28])[N:4]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][S:38][CH2:39][CH2:40][CH2:41][C:42]([F:48])([F:47])[C:43]([F:44])([F:45])[F:46]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of HCl in ethyl ether (2N, 3 ml) is added in 31-ml portions to a solution of Example 29 (250 mg, 0.36 mmole) in a CH2Cl2/AcOEt mixture (5 ml/3 ml) cooled down to 0° C., and the mixture is stirred for 60 hours at 23° C. The volatiles are evaporated off under vacuum and the residue is taken up in a CH2Cl2 (50 ml) and NaHCO3 (50 ml) mixture. After stirring and decantation, the organic phase is washed with water (50 ml) followed by salt water. After drying over Na2SO4, filtration and concentration to dryness, the residue is purified on a silica column (Heptane/AcOEt:10/0 to 1/1). The expected product is obtained in the form of a white solid with a yield of 76%. Melting point: 102-104° C.

Workup

customThe volatiles are evaporated off under vacuum
stirringAfter stirring
washdecantation, the organic phase is washed with water (50 ml)
dry with materialAfter drying over Na2SO4, filtration and concentration to dryness
customthe residue is purified on a silica column (Heptane/AcOEt:10/0 to 1/1)

Sources & evidence

ORD record: ord-77e5e8f591b04f6985924204104dd802
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710091B2

Reaction notes

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