N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → HCID 87376746, compound

HRID 1677614Notes

Reaction equation

HRID 1677614 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([CH2:11][S:12][C:13](=[O:15])[CH3:14])[C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[CH3:16][C:17]([O:20][C:21]([NH:23][CH2:24][C:25](ON1C(=O)CCC1=O)=[O:26])=[O:22])([CH3:19])[CH3:18]>O1CCOCC1>[C:17]([O:20][C:21]([NH:23][CH2:24][C:25]([N:1]1[CH2:2][CH2:3][CH:4]([CH:7]([CH2:11][S:12][C:13](=[O:15])[CH3:14])[C:8]([OH:10])=[O:9])[CH2:5][CH2:6]1)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 86608787HCID 86608787, compound

Product 1

HCID 87376746HCID 87376746, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(piperidin-4-yl)-3-(acetylthio)propanoic acid (0.6 g, 1.72 mmol) and Boc-glycine-N-hydroxysuccinimide ester (0.52 g, 1.9 mmol) was stirred in 15 mL of dioxane for 18 hours. The reaction mixture was concentrated, partitioned between ethyl acetate and 1 M NaHSO4. The organic layer was concentrated to give 2-(1-(t-butoxycarbonylaminomethylcarbonyl)-piperidin-4-yl)-3-(acetylthio)propanoic acid, which was dissolved in 10 mL of 1:1 methylene chloride-TFA for 1 hour. The reaction mixture was then concentrated. The resulting residue was dissolved in water-methanol, cooled to 0° C. and purged with nitrogen gas. Aqueous NH4OH was added and the resulting reaction mixture was stirred for 1 hour and then concentrated to an oil. Purification by prep HPLC afforded 65 mg of 2-(1-(aminomethylcarbonyl)-piperidin-4-yl)-3-mercaptopropanoic acid; NMR (D2O) 1.2-1.21 (m, 2), 1.51-1.82 (m, 3), 2.30-2.40 (m, 1), 2.48-2.71 (m, 2), 2.90-3.00 (m, 1), 3.55 (m, 1), 3.82 (m, 2), 4.21 (m, 1) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and 1 M NaHSO4
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-5a9be4fcc6d5461db6ca51d5f996abeb
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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