Hexanoic Acid → HCID 54233092, compound

HRID 1065544Notes

Reaction equation

HRID 1065544 reaction equation
C(OC(=O)C(C(C)C)CC(O)=O)C.[C:14]([NH:22][CH:23](CC1C=CC=CC=1)[C:24](=[O:33])[CH2:25][CH:26]([CH:30]([CH3:32])[CH3:31])[C:27]([OH:29])=[O:28])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:41]([OH:48])(=O)[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(OC(=O)[C@@H]1CCCN1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.O[N:65]1C2C=CC=CC=2N=N1>[Pd]>[C:14]([NH:22][CH:23]1[N:65]([C:41](=[O:48])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@:26]([CH:30]([CH3:31])[CH3:32])([C:27]([OH:29])=[O:28])[CH2:25][C:24]1=[O:33])(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 8892Hexanoic AcidHCID 757711-HydroxybenzotriazoleHCID 736155Benzyl L-prolinateHCID 9815473HCID 9815473, compoundHCID 20540789HCID 20540789, compound

Product 1

HCID 54233092HCID 54233092, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The 2-isopropylsuccinic acid 1-ethyl ester was converted into the 4-acid chloride as in Step 2, Example XIII and condensed with 2-phenyl-4-benzyloxazolone, and the resultant product subsequently was decarboxylated and hydrolyzed to 5-benzamido-4-oxo-2-isopropyl-6-phenylhexanoic acid as in Steps 3-4, Example XIII. The intermediate hexanoic acid was condensed with L-proline benzyl ester in a manner similar to Step 8, Example I, Procedure A, except that 1-hydroxybenzotriazole was omitted. The resultant mixture of diastereomeric proline benzyl esters was hydrogenated over 10% palladium-on-carbon in 90% yield to afford 5-benzamido-4-oxo-2-isopropyl-6-phenylhexanoyl-L-proline as a isomeric mixture whose mass spectrum showed a peak at m/e 464 in agreement with the calculated molecular weight. Calcd (C27H32N2O5.H2O) C, 67.2; H, 7.10; N, 5.80. Found: C, 66.8; H, 6.60; N, 5.90.

Sources & evidence

ORD record
ord-f13ba98c7f614292af80d8579c0a49d7
Source dataset
uspto-grants-1982_05
Patent number
US04329473

Reaction notes

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