4-Methylmorpholine → N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

HRID 2297064Notes

Reaction equation

HRID 2297064 reaction equation
N[C@H](C([CH:8]([CH:16]([NH2:31])[CH:17]([OH:30])[CH2:18][O:19][C:20]1[C:25]([F:26])=[C:24]([F:27])[CH:23]=[C:22]([F:28])[C:21]=1[F:29])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=O)C(C)C.[CH3:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[C:34]1[C:42]([OH:44])=O.C[N:46]1[CH2:51][CH2:50][O:49]CC1.[CH:52]1[CH:53]=CC2N(O)N=NC=2[CH:57]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[C:34]1[C:42]([NH:46][C@H:51]([C:50]([NH:31][CH:16]([CH:17]([OH:30])[CH2:18][O:19][C:20]1[C:21]([F:29])=[C:22]([F:28])[CH:23]=[C:24]([F:27])[C:25]=1[F:26])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:49])[CH:52]([CH3:53])[CH3:57])=[O:44]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 757711-HydroxybenzotriazoleHCID 131723667valinyl-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Product 1

HCID 86756371N-[(1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl esterYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 77 was followed using the product of Example 106 (197.0 mg, 0.44 mmol), 1-methylindole-2-carboxylic acid (152 mg, 0.87 mmol), NMM (0.047 ml, 0.44 mmol), HOBt (144 mg, 0.96 mmol), and EDAC (183 mg, 0.96 mmol) in methylene chloride to prepare the titled product (156 mg, 58%).

Sources & evidence

ORD record
ord-7322b7ff3f7f41098a43edd75890883c
Source dataset
uspto-grants-2002_12
Patent number
US06489353B2

Reaction notes

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