HCID 69818043, compound → HCID 69818012, compound

HRID 2417449Notes

Reaction equation

HRID 2417449 reaction equation
[OH:1][C@H:2]([CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:3][N:4]([C@@H:12]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[CH:29]=[CH:28][NH:27][CH:26]=2)=[O:24])=[CH:18][CH:17]=1)[CH2:13][OH:14])C(=O)OC(C)(C)C>Cl.C(O)C>[OH:14][CH2:13][C@@H:12]([NH:4][CH2:3][C@H:2]([OH:1])[CH2:30][O:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[CH:29]=[CH:28][NH:27][CH:26]=2)=[O:24])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 69818043HCID 69818043, compound

Product 1

HCID 69818012HCID 69818012, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

In 4N hydrogen chloride in ethanol (2.0 ml), tert-butyl N-[(2S)-2-hydroxy-3-phenoxypropyl]-N-[(1S)-2-hydroxy-1-[4-[(1H-pyrrol-3-ylcarbonyl)amino]benzyl]ethyl]carbamate (113.5 mg) was dissolved and the solution was stirred at room temperature for 30 hours. After concentration under reduced pressure, the residue was extracted with ethyl acetate (20 ml) and washed with saturated sodium hydrogencarbonate aqueous solution (20 ml). The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with brine, and dried over magnesium sulfate to give N-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]propyl]-phenyl]-1H-pyrrole-3-carboxamide (18.2 mg) as a yellow solid.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate (20 ml)
  3. washwashed with saturated sodium hydrogencarbonate aqueous solution (20 ml)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with ethyl acetate (20 ml)
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-b0bd0d9210894543a8c7d7f880230e0d
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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