Hydrochloric Acid → Methyl 4-{methyl[4-(pyrrolidin-1-yl)but-2-yn-1-yl]amino}-4-oxobutanoate

HRID 327802Notes

Reaction equation

HRID 327802 reaction equation
Cl.[CH3:2][N:3]([CH2:11][C:12]#[C:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH3:20]O>>[CH3:2][N:3]([CH2:11][C:12]#[C:13][CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)[C:4](=[O:10])[CH2:5][CH2:6][C:7]([O:9][CH3:20])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 551031HCID 551031, compound

Product 1

HCID 550731Methyl 4-{methyl[4-(pyrrolidin-1-yl)but-2-yn-1-yl]amino}-4-oxobutanoateYield 63%

Procedure

Dowex 50 resin (200 mg) which had been activated with HCl was added to a solution of N-Methyl-N-[4-(1-pyrrolidinyl)-2-butynyl]-3-carboxypropanamide (101 mg, 0.40 mmol) in MeOH (2 mL) and the suspension was vigorously stirred overnight. The resin was filtered off and washed thoroughly with TFA. The combined MeOH and TFA washes were evaporated under a stream of N2, neutralized with 2M Na2CO3 solution and the product was extracted into EtOAc (3× mL). The organic layer was dried over Na2CO3, evaporated in vacuo and purified on silica gel (CHCl3 /MeOH/NH4OH, 40/10/1) to give 009 (66.8 mg, 63% yield). MS (CI-NH3), m/e 267 (MH+), 186, 172. 1H NMR (CDCl3) δ1.79 (br s, 4 H), 2.58 (br s, 4 H), 2.64 (m, 4 H), 2.98 & 3.07* (s, 3 H), 3.38 (s, 2 H), 3.68 (s, 3 H), 4.08 & 4.24* (s, 2 H).

Workup

  1. filtrationThe resin was filtered off
  2. washwashed thoroughly with TFA
  3. customThe combined MeOH and TFA washes were evaporated under a stream of N2
  4. extractionthe product was extracted into EtOAc (3× mL)
  5. dry with materialThe organic layer was dried over Na2CO3
  6. customevaporated in vacuo
  7. custompurified on silica gel (CHCl3 /MeOH/NH4OH, 40/10/1)

Sources & evidence

ORD record
ord-d4aec2c0b3d34242af319a54195b12f6
Source dataset
uspto-grants-1993_12
Patent number
US05274121

Reaction notes

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