Morpholine → HCID 59223153, compound

HRID 539136Notes

Reaction equation

HRID 539136 reaction equation
C([O:4][C:5](=[O:55])[CH2:6][C@H:7]([OH:54])[C@H:8]([NH:12][C:13](=[O:53])[C@H:14]([NH:16][C:17](=[O:52])[C@H:18]([NH:22][C:23](=[O:51])[CH2:24][C@H:25]([OH:50])/[CH:26]=[CH:27]/[CH2:28][CH2:29][S:30][C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:19]([CH3:21])[CH3:20])[CH3:15])[CH:9]([CH3:11])[CH3:10])C=C.N1CCOCC1>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:54][C@H:7]([C@H:8]([NH:12][C:13](=[O:53])[C@H:14]([NH:16][C:17](=[O:52])[C@H:18]([NH:22][C:23](=[O:51])[CH2:24][C@H:25]([OH:50])/[CH:26]=[CH:27]/[CH2:28][CH2:29][S:30][C:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:19]([CH3:20])[CH3:21])[CH3:15])[CH:9]([CH3:11])[CH3:10])[CH2:6][C:5]([OH:55])=[O:4]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 59223145(3S,4R)-3-Hydroxy-4-{(R)-2-[(R)-2-((E)-(S)-3-hydroxy-7-tritylsulfanyl-hept-4-enoylamino)-3-methyl-butyrylamino]-propionylamino}-5-methyl-hexanoic acid allyl ester

Product 1

HCID 59223153HCID 59223153, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7 (152.2 mg, 0.2 mmol), Pd(PPh3)4 (23.2 mg, 0.02 mmol) in dry methanol (6 mL) under argon was added morpholine (35 μL, 0.40 mmol) which was allowed to stir for 2 h. The reaction mixture was concentrated in vacuo, purification by column chromatography on silica (eluent 0:1-5:95-10:90-10:90+0.5% AcOH MeOH/CH2Cl2) to give a yellow solid 8 (137 mg, 0.18 mmol, 100%): Rf 0.19 MeOH/CH2Cl2 (1:9+0.5% AcOH); IR (thin film) 3271 (b), 2962 (m), 2926 (m), 1624 (s), 1536 (m) cm−1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, purification by column chromatography on silica (eluent 0:1-5:95-10:90-10:90+0.5% AcOH MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e17863cda9fa4514bd3051780909d987
Source dataset
uspto-grants-2014_10
Patent number
US08865655B2

Reaction notes

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