D(-)-Leucinol → HCID 69482476, compound

HRID 2364209Notes

Reaction equation

HRID 2364209 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31](OCC)=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:37][C@H:38]([CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:39][OH:40]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31]([NH:37][C@@H:38]([CH2:39][OH:40])[CH2:41][CH:42]([CH3:44])[CH3:43])=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2724002D(-)-LeucinolHCID 69481817HCID 69481817, compound

Product 1

HCID 69482476HCID 69482476, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (2R)-2-amino-4-methyl-1-pentanol using methods similar to Example 563 to provide a pink solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90 (dd, J=6.42, 1.79 Hz, 6 H), 1.39-1.49 (m, 2 H), 1.55 (d, J=5.48 Hz, 4 H), 1.59-1.75 (m, 5 H), 2.35-2.45 (m, 2 H), 3.37 (d, J=8.00 Hz, 2 H), 3.40 (s, 2 H), 3.48 (s, 2 H), 4.04-4.13 (m, 1 H), 4.19 (s, 4 H), 4.93 (s, 1 H), 7.11-7.18 (m, 2 H), 7.41 (dd, J=8.74, 5.58 Hz, 2 H), 7.99 (s, 1 H), 8.56 (d, J=1.47 Hz, 1 H), 10.31 (d, J=8.63 Hz, 1 H), 17.26 (s, 1 H); ES+ MS: 567 (M+H+).

Workup

  1. customto provide a pink solid

Sources & evidence

ORD record
ord-be46f1b9d5714dea9061ed9713426a50
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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