Water → HCID 59656362, compound

HRID 1726465Notes

Reaction equation

HRID 1726465 reaction equation
C([O:3][C:4]([C@H:6]1[C@@H:11]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[CH2:7]1)=[O:5])C.C(OC(N1CCC(N)CC1)=O)(C)(C)C.N(C(C)C)=C=O.[OH-].[Li+].O>C1COCC1>[C:36]([N:8]1[CH2:9][CH2:10][C@H:11]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:18][CH:17]=2)(=[O:14])=[O:15])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)(=[O:40])[CH2:37][CH2:38][CH3:39]

Participants

7

Reactant 5

HCID 962WaterHCID 3939Lithium HydroxideHCID 61277Isopropyl isocyanateHCID 12682914-Amino-1-Boc-piperidineHCID 86594773HCID 86594773, compound2×

Product 1

HCID 59656362HCID 59656362, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-(cis)-1-Butyryl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-3-carboxylic acid ethyl ester was made following general procedure in Scheme 5, substituting (±)4-amino-1-benzyl-piperidine-3-carboxylic acid ethyl ester (5) for 4-amino-piperidine-1-carboxylic acid tert-butyl ester and substituting butyl chloride for 2-isocyanato-propane. To the solution of (±)-(cis)-1-butyryl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-3-carboxylic acid ethyl ester (70 mg, 0.12 mmol) in THF (5 mL), was added lithium hydroxide in water solution (6 mg, 0.25 mmol) and the resultant solution was stired at 25° C. for 2 h. The reaction mixture was extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to provide the crude product. HPLC purification of the residue gave the title compound. 1H NMR (300 MHz, DMSO) δ 10.62 (s, 1H), 8.77 (t, 1H), 8.24 (m, 3H), 7.95 (d, 1H), 7.70 (m, 3H), 7.38 (m, 3H), 3.72 (m, 2H), 3.35 (m, 6H), 3.12 (m, 1H), 2.60 (m, 1H), 2.15 (m, 2H), 1.32 (m, 4H), 0.80 (dd, 3H); LC/MS nm/z 539 (M+H)+

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide the crude product
  7. customHPLC purification of the residue

Sources & evidence

ORD record
ord-3247586c2d114f3eaf1abf822757a91d
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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