Methylamine → HCID 69900398, compound

HRID 1278741Notes

Reaction equation

HRID 1278741 reaction equation
C(O[C:5]([CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[O:6])(C)C.[CH3:31][NH2:32]>>[CH3:31][NH:32][C:5]([CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:14])=[O:6]

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 699000221-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzenesulfonyl]-pyrrolidine-2-carboxylic acid isopropyl ester

Product 1

HCID 69900398HCID 69900398, compound

Procedure

0.57 g of 1-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzenesulfonyl]-pyrrolidine-2-carboxylic acid isopropyl ester ( ) was stirred in 20 mL methyl amine (40% wt in water) at 100° C. in a sealed tube for 5 days. The methyl amine was allowed to evaporate and the residual aqueous solution was left to stand overnight uncapped. The following morning, a white precipitate was present, which was collected by vacuum filtration. The precipitate was washed with water and hexanes. The original aqueous solution was then extracted twice with ethyl acetate. The organic layer was then dried over sodium sulfate and concentrated in vacuo to afford more product. 0.31 g of the title compound was collected as a white solid; mp 137-139° C.; 1H NMR (CDCl3) δ 1.52-1.72 (m, 5H), 1.81 (t, J=5.82 Hz, 4H), 2.15-2.20 (m, 1H), 2.86 (d, J=4.95 Hz, 3H), 3.08-3.55 (m, 1H), 3.49-3.55 (m, 4H), 4.00 (s, 4H), 6.89-6.94 (M, 2H), 6.99-7.01 (m, 1H), 7.61-7.73 (m, 2H); MS (ES) m/z 410.0 (MH+); HRMS for C19H27N3O5S: 410.1740.

Workup

  1. customto evaporate
  2. waitthe residual aqueous solution was left
  3. filtrationwhich was collected by vacuum filtration
  4. washThe precipitate was washed with water and hexanes
  5. extractionThe original aqueous solution was then extracted twice with ethyl acetate
  6. dry with materialThe organic layer was then dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford more product
  9. custom0.31 g of the title compound was collected as a white solid

Sources & evidence

ORD record
ord-0a3188e4f4d2409eb4cd5a49d6061f2c
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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