Isopropyl isocyanate → HCID 86594775, compound

HRID 1726468Notes

Reaction equation

HRID 1726468 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@@H:9]([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:8]([C:36](OCC)=[O:37])[CH2:7]1)=[O:5])[CH3:2].C(OC(N1CCC(N)CC1)=O)(C)(C)C.N(C(C)C)=C=O.[BH4-].[Li+]>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@@H:9]([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:8]([CH2:36][OH:37])[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 61277Isopropyl isocyanateHCID 12682914-Amino-1-Boc-piperidineHCID 4148881Lithium borohydrideHCID 86594776HCID 86594776, compound2×

Product 1

HCID 86594775HCID 86594775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(±)-(trans)-4-[4-(2-Methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1,3-dicarboxylic acid diethyl 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 ethyl chloroformate for 2-isocyanato-propane. To the solution of (±)-(trans)-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1,3-dicarboxylic acid diethyl ester (57 mg, 0.1 mmol) in THF (5 mL), was added lithium borohydride in THF solution (0.5 mL, 0.25 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 8.73 (d, 1H), 8.30 (d, 1H), 8.22 (d, 1H), 7.93 (d, 1H), 7.68 (m, 3H), 7.36 (m, 3H), 4.15 (d, 1H), 4.05 (q, 2H), 3.85 (d, 1H), 3.55 (d, 1H), 3.25 (m, 1H), 3.10 (m, 1H), 2.60 (m, 2H), 2.56 (s, 3H), 1.40 (m, 3H), 1.20 (t, 3H); LC/MS m/z 526 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-863abcc9247d413482971516a2231409
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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