Ethanolamine → HCID 77768207, compound

HRID 2230325Notes

Reaction equation

HRID 2230325 reaction equation
N1(C(C([NH:12][CH:13]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:14]([NH:16][CH:17]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[C:18]([OH:20])=O)=[O:15])=O)=O)CCCCCC1.[OH:40][CH2:41][CH2:42][NH2:43].[CH3:44][N:45]([CH:47]=[O:48])[CH3:46]>>[CH2:29]([O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH:17]([NH:16][C:14]([CH:13]([NH:12][C:47]([N:45]2[CH2:46][CH2:37][CH2:36][CH2:13][CH2:14][CH2:44]2)=[O:48])[CH2:36][CH:37]([CH3:39])[CH3:38])=[O:15])[C:18](=[O:20])[NH:43][CH2:42][CH2:41][OH:40])=[CH:27][CH:26]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 6228DimethylformamideHCID 18464352HCID 18464352, compound

Product 1

HCID 77768207HCID 77768207, compound

Procedure

A suspension of the resin prepared in Example AS (2-{2[(Azepane-1-carbonyl-carbonyl)-amino]-4-methyl-pentanoylamino }-3-(4-benzyloxy-phenyl) propionic acid kaiser oxime resin ester) (0.5 g, load Å 0.3-0.5 mmol/g resin) in 4 mL of DMF was treated with 2-hydroxyethylamine (2.5 mmol). The resulting suspension was shaken overnight, and the resin was removed by filtration. The resin was washed with additional DMF, and the combined solvent was removed under vacuum. The residue was dissolved in CH2Cl2 or ethyl acetate and washed with aqueous 0.5N HCl solution. The organic phase was dried and concentrated. The residue was purified give the title compound by preparative HPLC using the following conditions:

Workup

  1. additionA suspension of the resin
  2. customthe resin was removed by filtration
  3. washThe resin was washed with additional DMF
  4. customthe combined solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washethyl acetate and washed with aqueous 0.5N HCl solution
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-8457fdd129594386b3270685b24a762c
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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