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

HRID 2384051Notes

Reaction equation

HRID 2384051 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-4c51528a5ff74415834b4cdbe3702083
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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