2-[N-tert-butoxycarbonyl-N-{3-methoxycarbonyl-1-[3-(2-propenyloxycarbonylamino)phenyl]propyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine → 2-[N-tert-butoxycarbonyl-N-{4-hydroxy-1-[3-(2-propenyloxycarbonylamino)phenyl]butyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine

HRID 849236Notes

Reaction equation

HRID 849236 reaction equation
[C:1]([O:5][C:6]([N:8]([C:29]1[CH:34]=[C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:32]=[C:31]([CH2:41][S:42][C:43]2[S:44][C:45]([CH2:48][CH3:49])=[N:46][N:47]=2)[N:30]=1)[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH:17]=1)[CH2:10][CH2:11][C:12](OC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].O1CCCC1>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:29]1[CH:34]=[C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:32]=[C:31]([CH2:41][S:42][C:43]2[S:44][C:45]([CH2:48][CH3:49])=[N:46][N:47]=2)[N:30]=1)[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH:17]=1)[CH2:10][CH2:11][CH2:12][OH:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 193696512-[N-tert-butoxycarbonyl-N-{3-methoxycarbonyl-1-[3-(2-propenyloxycarbonylamino)phenyl]propyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridineHCID 131718764lithium borohydride THF

Product 1

HCID 193696602-[N-tert-butoxycarbonyl-N-{4-hydroxy-1-[3-(2-propenyloxycarbonylamino)phenyl]butyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[N-tert-butoxycarbonyl-N-{3-methoxycarbonyl-1-[3-(2-propenyloxycarbonylamino)phenyl]propyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine (100 mg) obtained in Example 138-(2) was dissolved in tetrahydrofuran (3 ml), and a 2 M lithium borohydride-tetrahydrofuran solution (0.1 ml) was added thereto, followed by stirring at room temperature for 15 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to obtain the above identified compound (66 mg).

Workup

  1. washwashed with a saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)
  5. customto obtain the

Sources & evidence

ORD record
ord-bd6eacf139d743588235379563ad4118
Source dataset
uspto-grants-2000_01
Patent number
US06011039

Reaction notes

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