Dichloromethane → HCID 131729731, compound

HRID 1926703Notes

Reaction equation

HRID 1926703 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:15]=2)[N:10]([OH:27])[C:9]1=[O:28])(C)(C)C.N[C@H]1CC2C(=NC=C(OC3C=CC=CC=3)C=2)N(O)C1=O.C(Cl)[Cl:51]>>[NH2:7][C@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:15]=2)[N:10]([OH:27])[CH2:9]1.[ClH:51].[NH2:7][C@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:19])=[O:20])[CH:15]=2)[N:10]([OH:27])[C:9]1=[O:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 59627130HCID 59627130, compoundHCID 59627148HCID 59627148, compound

Product 2

HCID 131729731HCID 131729731, compoundHCID 131729732HCID 131729732, compound

Procedure

(3S)-3-Amino-1-hydroxy-6-(phenylsulfonyl)-3,4-dihydroquinolin-2(1H-one, hydrochloride salt (72) Compound 72 was prepared from tert-butyl [(3S)-1-hydroxy-2-oxo-6-(phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-yl]carbamate (71) according to the general procedure for the synthesis of (3S)-3-amino-1-hydroxy-6-phenoxy-3,4-dihydro-1,8-naphthyridin-2(1H)-one (67) in Example 66, except that the neutral product (15 mg, 34%) was converted to its hydrochloride salt by dissolution in DCM and treatment with 2 N HCl in Et2O, followed by removal of solvent in vacuo. The product was obtained as a solid. Characterization data was obtained on the neutral form of the product. LCMS m/z 318.9 (M+1). 1H NMR (500 MHz, CDCl3) δ 2.81-2.94 (m, 1H), 3.01-3.13 (m, 1H), 3.65-3.79 (br s, 1H), 4.3-5.1 (v br s, 3H), 7.28-7.35 (m, 1H), 7.49-7.54 (m, 2H), 7.55-7.60 (m, 1H), 7.67 (br s, 1H), 7.73-7.79 (m, 1H), 7.91 (br d, J=7.3 Hz, 2H).

Workup

  1. customtreatment with 2 N HCl in Et2O, followed by removal of solvent in vacuo
  2. customThe product was obtained as a solid
  3. customCharacterization data was obtained on the neutral form of the product

Sources & evidence

ORD record
ord-638052f7542e4809bf7bbd616eb530d6
Source dataset
uspto-grants-2012_05
Patent number
US08183238B2

Reaction notes

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