Water → HCID 9865107, compound

HRID 1740838Notes

Reaction equation

HRID 1740838 reaction equation
[OH2:1].[O:2]=[C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:6][CH:5](CCN2CCC(C(O)=O)CC2)[O:4]1.[OH-].[Na+].[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[O:2]=[C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:6][C@H:5]([CH2:3][N:7]2[CH2:6][CH2:5][CH:36]([C:37]([OH:33])=[O:1])[CH2:35][CH2:34]2)[O:4]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21833614HCID 21833614, compound

Product 1

HCID 9865107HCID 9865107, compound

Procedure

A solution of 230 mg of the ethyl ester prepared in e) in 2 ml tetrahydrofuran and 1 ml water is admixed with 0.7 ml 1 n sodium hydroxide solution and stirred for 1 h at room temperature. Subsequently the tetrahydrofuran is removed in a vacuum and the product is purified by means of an ion exchanger (Dowex 50, H form). 120 mg of the title compound is obtained in this way as a white powder. FAB=388; 1H-NMR (d6 -DMSO) δ=8.15 ppm (d, 2H); 6.82 (d, 2H); 4.60 (m, 1H); 4.02 (broad d, 2H); 3.75 (m, 1H); 3.50 (t, 1H); 3.15 (dd, 1H); 2.95 (broad d, 2H); 2.80 (m, 2H); 2.52 (m, 2H); 2.10 (m, 3H); 1.80-1.40 (m, 8H).

Workup

  1. customSubsequently the tetrahydrofuran is removed in a vacuum
  2. customthe product is purified by means of an ion exchanger (Dowex 50, H form)

Sources & evidence

ORD record
ord-3f9b7ef53cb3425ebf2b5227bc8bb84b
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

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