(S)-N-[2-[2-(R)-(1,1-dimethylethyloxycarbonylamino)-3-phenylpropionyloxy]-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate → (+)-N-[2-hydroxyl-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate

HRID 19754Notes

Reaction equation

HRID 19754 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].CC(C)(OC(N[C@H](CC1C=CC=CC=1)C([O:19][C@@H:20]([CH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:21][O:22][N:23]=[C:24]([Cl:31])[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=O)=O)C>CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[OH:19][CH:20]([CH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:21][O:22][N:23]=[C:24]([Cl:31])[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 86761136(S)-N-[2-[2-(R)-(1,1-dimethylethyloxycarbonylamino)-3-phenylpropionyloxy]-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate

Product 1

HCID 86761135(+)-N-[2-hydroxyl-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.16 g (3.26 mmole) of (S)—N-[2-[2-(R)-(1,1-dimethylethyloxycarbonylamino)-3-phenylpropionyloxy]-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate (1:1) (see Example 18) was suspended in 40 ml of methanol and boiled for 1 hour, then evaporated to dryness. The residue was triturated with 20 ml of ethyl acetate, the precipitate was filtered, washed with ethyl acetate. This crude product was recrystallized in isopropyl alcohol to yield the title compound.

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with 20 ml of ethyl acetate
  3. filtrationthe precipitate was filtered
  4. washwashed with ethyl acetate
  5. customThis crude product was recrystallized in isopropyl alcohol

Sources & evidence

ORD record
ord-afa64d52367f455f994cd777e6d6b289
Source dataset
uspto-grants-2010_06
Patent number
US07745465B2

Reaction notes

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