Hydrochloric Acid → HCID 69751369, compound

HRID 497466Notes

Reaction equation

HRID 497466 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][C@@H:7]1[NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:5])C.[OH-].[Li+].Cl>O1CCCC1>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C@H:6]([C:4]([OH:5])=[O:3])[C@@H:7]([NH:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:8]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69748562HCID 69748562, compound

Product 1

HCID 69751369HCID 69751369, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask (3R,4S)-3-benzyloxycarbonylamino-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (1.19 g, 2.93 mmol) was dissolved in tetrahydrofuran (48 mL) and lithium hydroxide (12 mL of a 1N aqueous solution, 15 mmol) was added. The mixture was stirred for 60 hours. The reaction mixture was acidified with aqueous hydrochloric acid (3 mL of a 2M solution) and then extracted with ethyl acetate three times (30 mL). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to give a crude white solid (1.13 g) which was used without further purification. 1H NMR (300 MHz, CDCl3), δ: 7.35 (m, 5H), 5.10 (m, 2H), 3.91, (m, 2H), 3.19 (m, 1H), 2.71 (m, 2H), 1.92 (m, 1H), 1.74 (m, 2H), 1.45 (s, 9H). MS (APCI), m+/z: (M+H)+=379.

Workup

  1. extractionthen extracted with ethyl acetate three times (30 mL)
  2. dry with materialThe combined organic layers were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-842a6166adae414897db3775bf5b30ca
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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