Acetic Acid → HCID 16035070, compound

HRID 2234181Notes

Reaction equation

HRID 2234181 reaction equation
O=[CH:2][CH2:3][N:4]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:5](=[O:17])[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[NH2:33][CH2:34][CH2:35][C:36]1[C:44]2[S:43][C:42](=[O:45])[NH:41][C:40]=2[C:39]([OH:46])=[CH:38][CH:37]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[OH:46][C:39]1[C:40]2[NH:41][C:42](=[O:45])[S:43][C:44]=2[C:36]([CH2:35][CH2:34][NH:33][CH2:2][CH2:3][N:4]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:5](=[O:17])[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochlorideHCID 86625180HCID 86625180, compound

Product 1

HCID 16035070HCID 16035070, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(2-Oxoethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide (Example 9c), 0.12 g) was dissolved in methanol (5 mL) and treated with 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.32 g), acetic acid (0.1 mL) and water (0.3 mL). The resultant mixture was stirred for 2 hours and then sodium cyanoborohydride (0.01 g) was added and the reaction mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in methanol (5 mL) and adsorbed onto silica gel. The product was purified by flash chromatography eluting with 5% methanol, 1% ammonia in dichloromethane. Collected fractions were concentrated and the resultant residue was taken up in dichloromethane (5 mL) and treated with 4N hydrogen chloride in dioxane (0.2 mL). The mixture was stirred vigorously and concentrated. The resulting gum was azeotroped with dichloromethane (3×5 mL) to give the titled compound (0.13 g) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe product was purified by flash chromatography
  3. washeluting with 5% methanol, 1% ammonia in dichloromethane
  4. concentrationCollected fractions were concentrated
  5. additiontreated with 4N hydrogen chloride in dioxane (0.2 mL)
  6. stirringThe mixture was stirred vigorously
  7. concentrationconcentrated
  8. customThe resulting gum was azeotroped with dichloromethane (3×5 mL)

Sources & evidence

ORD record
ord-9bd2789dc74b4e079d95746dd87d6b81
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

Loading…