Triethylamine → (2R,4S)-5-Biphenyl-4-yl-2-methyl-4-(1H-tetrazol-5-ylcarbamoyl)-pentanoic acid ethyl ester

HRID 1469629Notes

Reaction equation

HRID 1469629 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:24])[C@H:6]([CH3:23])[CH2:7][C@H:8](N)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH3:3].Cl.C(O[C:29](=[O:49])[C@@H](C)CC(N)CC1C=CC(C2C=CC=C(Cl)C=2)=CC=1)C.CC[N:52](CC)CC.CN(C(O[N:65]1[N:73]=[N:72]C2C=CC=[N:71][C:66]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>[Pd].CN(C=O)C.C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:24])[C@H:6]([CH3:23])[CH2:7][C@H:8]([C:29](=[O:49])[NH:71][C:66]1[NH:52][N:72]=[N:73][N:65]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25017086(2R,4S)-4-amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochlorideHCID 67505771HCID 67505771, compound

Product 1

HCID 178472550(2R,4S)-5-Biphenyl-4-yl-2-methyl-4-(1H-tetrazol-5-ylcarbamoyl)-pentanoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared using similar procedure described in Example 52-1 with appropriate intermediates and conditions. Intermediate 1 and benzyl-H-tetrazole-5-carbonyl chloride (prepared according to J. Med. Chem. 1986, 29, 538-549) are used instead of intermediates 31 and 32. For coupling reaction, Et3N and DCM are used instead of HATU and DMF. For deprotection, hydrogeneation with Pd on carbon is used instead of TFA.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-91a384849d6342a18903e1f4ff5a1853
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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