Methanol → (+/-)-3-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-yl]-3-[4-(7-methoxy-quinolin-8-yl)-[1,4]diazepan-1-yl]-propionic acid

HRID 2063565Notes

Reaction equation

HRID 2063565 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH:5]([C:25]1[N:26]=[C:27]([N:30]2[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]2)[S:28][CH:29]=1)[N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[C:14]([O:23][CH3:24])=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH2:8][CH2:7]1.[OH-].[Na+].CO>C1COCC1>[OH:36][CH:33]1[CH2:32][CH2:31][N:30]([C:27]2[S:28][CH:29]=[C:25]([CH:5]([N:6]3[CH2:12][CH2:11][CH2:10][N:9]([C:13]4[C:14]([O:23][CH3:24])=[CH:15][CH:16]=[C:17]5[C:22]=4[N:21]=[CH:20][CH:19]=[CH:18]5)[CH2:8][CH2:7]3)[CH2:4][C:3]([OH:37])=[O:2])[N:26]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59366202(+/-)-3-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-yl]-3-[4-(7-methoxy-quinolin-8-yl)-[1,4]diazepan-1-yl]-propionic acid methyl ester

Product 1

HCID 59366189(+/-)-3-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-yl]-3-[4-(7-methoxy-quinolin-8-yl)-[1,4]diazepan-1-yl]-propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step 1 (660 mg, 1.26 mmol) was dissolved in THF (4.20 mL) and 1 N aq. NaOH (2.52 mL, 2.52 mmol) was added, followed by MeOH (2.10 mL). The reaction was stirred at room temp for 3 h, then concentrated. The product was taken up in CH2Cl2 and water, then acidified to pH 4 with AcOH. NH4OH was added to bring the pH to 9, then the aqueous was extracted with CH2Cl2 (3×50 mL). The combined organic was dried over MgSO4, filtered, and concentrated to give the product, which was used without further purification.

Workup

  1. concentrationconcentrated
  2. additionNH4OH was added
  3. extractionthe aqueous was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-0d14e60185074a238e7b90b57ca539fb
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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