Isopropyl isocyanate → HCID 86594771, compound

HRID 1726464Notes

Reaction equation

HRID 1726464 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)C.C(OC(N1CCC(N)CC1)=O)(C)(C)C.N(C(C)C)=C=O.[BH4-].[Li+]>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:15])=[O:14])[C@H:6]([CH2:4][OH:3])[CH2:7]1)(=[O:40])[CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 61277Isopropyl isocyanateHCID 12682914-Amino-1-Boc-piperidineHCID 4148881Lithium borohydrideHCID 86594772HCID 86594772, compound2×

Product 1

HCID 86594771HCID 86594771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(±)-(trans)-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 (±)-(trans)-1-butyryl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-3-carboxylic acid ethyl ester (121 mg, 0.21 mmol) in THF (5 mL), was added lithium borohydride in THF solution (1.07 mL, 2.1 mmol) and the resultant solution was stired at 0° C. for 2 h. The solvent was removed in vacuo and the crude material was purified by HPLC to give the title compound. 1H NMR (300 MHz, MeOD) δ 8.75 (d, 1H), 8.32 (dd, 1H), 8.24 (d, 1H), 7.93 (d, 1H), 7.70 (m, 3H), 7.38 (m, 3H), 4.00 (m, 3H), 3.20 (m, 2H), 2.88 (m, 1H), 2.55 (s, 3H), 2.46 (m, 1H), 2.28 (m, 2H), 1.50 (m, 3H), 1.24 (m, 2H), 0.90 (dd, 3H); LC/MS m/z 525 (M+H)+

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material was purified by HPLC

Sources & evidence

ORD record
ord-b1539432cc6e4655a6c444982e7da9da
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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