Methanol → HCID 16035376, compound

HRID 2234190Notes

Reaction equation

HRID 2234190 reaction equation
[CH2:1]([N:8]([CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27]1[C:35]2[S:34][C:33](=[O:36])[NH:32][C:31]=2[C:30]([OH:37])=[CH:29][CH:28]=1)[C:9](=O)[CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[CH3:39]O>O1CCCC1>[OH:37][C:30]1[C:31]2[NH:32][C:33](=[O:36])[S:34][C:35]=2[C:27]([CH2:26][CH2:25][NH:24][CH2:23][CH2:22][N:8]([CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:1][CH2:2][C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:39]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 16036644HCID 16036644, compound

Product 1

HCID 16035376HCID 16035376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Benzyl-N-[2-[2-(4-hydroxy-2-oxo-3H-benzothiazol-7-yl)ethylamino]ethyl]-3-phenethyloxy-propanamide (Example 4, 0.1 g) was dissolved in tetrahydrofuran (6 mL) and treated with borane (1M in tetrahydrofuran, 1 mL) at room temperature. The resultant solution was heated at 50° C. for 3 hours. The reaction was then cooled to 0° C. and methanol (6 mL) was added dropwise. Following this, the mixture was concentrated and the collected residue was dissolved in methanol (6 mL) and treated with concentrated hydrochloric acid (1.6 mL). The acidic solution was heated at 60° C. for 14 hours, then cooled to room temperature and concentrated. The resulting residue was purified by preparative HPLC (95:05, ammonia (0.2%):acetonitrile) to give the titled compound (0.035 g) as a glass like solid.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe collected residue was dissolved in methanol (6 mL)
  3. additiontreated with concentrated hydrochloric acid (1.6 mL)
  4. temperatureThe acidic solution was heated at 60° C. for 14 hours
  5. temperaturecooled to room temperature
  6. concentrationconcentrated
  7. customThe resulting residue was purified by preparative HPLC (95:05, ammonia (0.2%):acetonitrile)

Sources & evidence

ORD record
ord-27708b6e850e4b06a7e887d94cf97d3b
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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