4-Methylmorpholine → HCID 58327285, compound

HRID 879886Notes

Reaction equation

HRID 879886 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[CH2:39][O:38][C:17]3=[CH:18][C:19]4[CH2:20][C@@H:21]([C:35](O)=[O:36])[N:22]([C@H:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:27][CH3:28])[CH2:23][C:24]=4[CH:25]=[C:16]3[O:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.C[O:43][C:44](=[O:62])[C@@H:45]([NH2:61])[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][N:56]=[C:55]([CH3:59])[C:54]=2[CH3:60])=[CH:49][CH:48]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.C(Cl)CCl>[CH3:59][C:55]1[C:54]([CH3:60])=[C:53]([C:50]2[CH:51]=[CH:52][C:47]([CH2:46][C@H:45]([NH:61][C:35]([C@@H:21]3[CH2:20][C:19]4[CH:18]=[C:17]5[O:38][CH2:39][C@H:14]([C:11]6[CH:10]=[CH:9][C:8]([O:1][C:2]7[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=7)=[CH:13][CH:12]=6)[O:15][C:16]5=[CH:25][C:24]=4[CH2:23][N:22]3[C@H:26]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:27][CH3:28])=[O:36])[C:44]([OH:43])=[O:62])=[CH:48][CH:49]=2)[CH:58]=[CH:57][N:56]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 66719267L-Phenylalanine, 4-(2,3-dimethyl-4-pyridinyl)-, methyl ester, hydrochloride (1:2)HCID 66719862HCID 66719862, compound

Product 1

HCID 58327285HCID 58327285, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

(3S,8S)-3-(4-Phenoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid (10 mg), (S)-2-amino-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester bis hydrochloride (8 mg), EDC (5 mg), and HOBt (3 mg) were suspended in 5 mL DCM and NMM (0.009 mL) added. The reaction mixture was stirred at room temperature for 6 hours and directly purified over silica (hexanes to 1:1 hexanes EtOAc to 1:1 hexanes EtOAc+1% MeOH). The resulting compound was hydrolyzed according to General Procedure B to give the title compound (9 mg). LCMS (m/z): 775.

Workup

  1. customdirectly purified over silica (hexanes to 1:1 hexanes EtOAc to 1:1 hexanes EtOAc+1% MeOH)

Sources & evidence

ORD record
ord-708e39989c3d4f26badec32dd415c96a
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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