Acetic Acid → HCID 11700600, compound

HRID 1670506Notes

Reaction equation

HRID 1670506 reaction equation
[CH2:1]=O.[C:3]([OH:6])(=O)[CH3:4].[C:7]([BH3-])#[N:8].[Na+].[Cl:11][C:12]1[CH:59]=[CH:58][C:15]([CH2:16][CH:17]2[N:22]3[C:23](=[O:53])[CH:24]([NH:38][C:39]([CH:41]4[CH2:45][CH2:44][CH2:43][N:42]4C(=O)C(N)C(C)C)=[O:40])[CH2:25][N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])(=[O:29])=[O:28])[CH:21]3[CH2:20][N:19]([CH:54]([CH3:56])[CH3:55])[C:18]2=[O:57])=[CH:14][CH:13]=1.[CH2:60]1[CH2:64]OC[CH2:61]1>CO.C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[N:22]3[C:23](=[O:53])[CH:24]([NH:38][C:39]([CH:41]4[CH2:45][CH2:44][CH2:43][N:42]4[C:3](=[O:6])[CH:4]([N:8]([CH3:7])[CH3:1])[CH:60]([CH3:64])[CH3:61])=[O:40])[CH2:25][N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])(=[O:29])=[O:28])[CH:21]3[CH2:20][N:19]([CH:54]([CH3:55])[CH3:56])[C:18]2=[O:57])=[CH:58][CH:59]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 11679362HCID 11679362, compound

Product 1

HCID 11700600HCID 11700600, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

15 μl of formaldehyde, 15 μl of glacial acetic acid and 62.8 μl of a 1M sodium cyanoborohydride solution in THF are added to a solution of 40 mg of N-[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]-1-(2-amino-3-methylbutyryl)pyrrolidine-2-carboxamide in 556 μl of methanol and 278 μl of methylene chloride. The reaction mixture is stirred at room temperature for 6 h. The solvent is then removed in vacuo, and the residue is taken up in ethyl acetate and water. The aqueous phase is extracted twice with ethyl acetate, and the combined organic phases are dried over sodium sulfate and filtered, and the solvent is removed in vacuo. The resulting crude product is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The desired product is obtained with MW=782.22 (calculated, monoisotopic); measured value (M+H)+: 783.35.

Workup

  1. customThe solvent is then removed in vacuo
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. customThe resulting crude product is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

Sources & evidence

ORD record
ord-12778f422a274b2ebd75464b43df68b3
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

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