Sodium Hydroxide → HCID 178467732, compound

HRID 323601Notes

Reaction equation

HRID 323601 reaction equation
C([O:3][C:4](=[O:35])[CH:5]([O:32][CH2:33][CH3:34])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][C:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21][C:20]3[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=3[N:18]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH:24]1[C:23]2[C:17]([NH:16][CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([O:32][CH2:33][CH3:34])[C:4]([OH:35])=[O:3])=[CH:12][CH:11]=3)=[N:18][C:19]3[CH:31]=[CH:30][CH:29]=[CH:28][C:20]=3[S:21][C:22]=2[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178471049HCID 178471049, compound

Product 1

HCID 178467732HCID 178467732, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-[2-(Dibenzo[b,f]-1,4-thiazepin-11-ylamino)-ethoxy]-phenyl)-2-ethoxy-propanoic acid ethyl ester (1.6 g, 3.26 mmol) was dissolved in ethanol (30 ml) and 20% sodium hydroxide (3 ml) was added. After 6 days ethanol was evaporated in vacuo, water (50 ml) and acetic acid (3 ml) were added, the product was filtered off and dried yielding 1.4 g (87%) of the title compound as hydrate. 1H NMR (250 MHz, DMSO-d6) δ7.3-7.6 (m, 6 H), 7.10-7.25 (m, 3 H), 6.82-7.15 (m+bs, 4-5 H), 4.26 (bt, J=4.9 Hz, 2 H), 3.88 (dd, J=7.6 Hz and 4.2 Hz, 1 H), 3.78 (bs, 2 H), 3.54 (m)+3.25 (m), 2 H; 2.91 (bdd, 1 H), 2.70-2.82 (m, 1 H), 1.03 (t, J=7.2 Hz, 3 H).

Workup

  1. customAfter 6 days ethanol was evaporated in vacuo, water (50 ml) and acetic acid (3 ml)
  2. additionwere added
  3. filtrationthe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-1943705194104bbd8034287c215413fb
Source dataset
uspto-grants-2001_04
Patent number
US06214820B1

Reaction notes

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