Methane → HCID 69756244, compound

HRID 480665Notes

Reaction equation

HRID 480665 reaction equation
[C:1](C(CCCCN)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.C([O:25][C:26](=[O:36])[C@@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH2:28])C1C=CC=CC=1.F[P-](F)(F)(F)(F)F.[N:44]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2N=N1.CCN(C(C)C)C(C)C.C.C([OH:76])C>[Pd]>[C:1]([N:28]([C:47](=[O:76])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][NH2:44])[C@@H:27]([C:26]([OH:25])=[O:36])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

8

Reactant 6

HCID 297MethaneHCID 702EthanolHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18470676HCID 18470676, compoundHCID 69754176HCID 69754176, compound

Product 1

HCID 69756244HCID 69756244, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

BOC-6-aminohexanoic acid (2.14 g, 9.25 mmol) was coupled to D-phenylalanine benzyl ester hydrochloride (2.7 g, 9.25 mmol) with Py-BOP in the presence of DIPEA, and the resulting product was hydrogenated in 95% ethanol at atmospheric pressure in the presence of 10% palladium over charcoal to afford BOC-6-aminohexanoyl-D-phenylalanine (3.35 g, 85%). The title compound was obtained by coupling BOC-6-aminohexanoyl-D-phenylalanine to Compound 2, deprotection and RP-HPLC as described for Compound 3.

Sources & evidence

ORD record
ord-c48a4c2ced7f479f8659021dd0961516
Source dataset
uspto-grants-2003_11
Patent number
US06653299B1

Reaction notes

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