2,6-Lutidine → Isobutyl 3-(Tert-Butyldisulfanyl)-1-(1-(Chloro(((2S,6R)-6-(5-Methyl-2,4-Dioxo-3,4-Dihydropyrimidin-1(2H)-yl)-4-Tritylmorpholin-2-yl)Methoxy)Phosphoryl)Piperidin-4-ylamino)-1-Oxopropan-2-ylcarbamate

HRID 923723Notes

Reaction equation

HRID 923723 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][N:7]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@H:5]([N:28]2[CH:33]=[C:32]([CH3:34])[C:31](=[O:35])[NH:30][C:29]2=[O:36])[O:4]1.N1C(C)=CC=CC=1C.[C:45]([S:49][S:50][CH2:51][CH:52]([NH:66][C:67](=[O:73])[O:68][CH2:69][CH:70]([CH3:72])[CH3:71])[C:53]([NH:55][CH:56]1[CH2:61][CH2:60][N:59]([P:62](Cl)([Cl:64])=[O:63])[CH2:58][CH2:57]1)=[O:54])([CH3:48])([CH3:47])[CH3:46]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:45]([S:49][S:50][CH2:51][CH:52]([NH:66][C:67](=[O:73])[O:68][CH2:69][CH:70]([CH3:71])[CH3:72])[C:53]([NH:55][CH:56]1[CH2:57][CH2:58][N:59]([P:62]([Cl:64])([O:1][CH2:2][C@H:3]2[O:4][C@@H:5]([N:28]3[CH:33]=[C:32]([CH3:34])[C:31](=[O:35])[NH:30][C:29]3=[O:36])[CH2:6][N:7]([C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:8]2)=[O:63])[CH2:60][CH2:61]1)=[O:54])([CH3:48])([CH3:47])[CH3:46]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 166621301-((2R,6S)-6-(Hydroxymethyl)-4-(triphenylmethyl)-2-morpholinyl)-5-methyl-2,4(1H,3H)-pyrimidinedioneHCID 87108177Isobutyl 3-(Tert-Butyldisulfanyl)-1-(1-(Dichlorophosphoryl)Piperidin-4-ylamino)-1-Oxopropan-2-ylcarbamate

Product 1

HCID 87107533Isobutyl 3-(Tert-Butyldisulfanyl)-1-(1-(Chloro(((2S,6R)-6-(5-Methyl-2,4-Dioxo-3,4-Dihydropyrimidin-1(2H)-yl)-4-Tritylmorpholin-2-yl)Methoxy)Phosphoryl)Piperidin-4-ylamino)-1-Oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (moT(Tr)) (5.576 g, 10.98 mmol) in DCM (100 ml) at 0° C., was added lutidine (1.92 ml, 16.47 mmol) and DMAP (669 mg, 5.5 mmol), followed by the addition of the compound from Example 62 (6.13 g, 12.08 mmol). The reaction was left stirring at RT for 18 h. The title compound was obtained after ISCO purification (50% EtAc/Hexane).

Workup

  1. waitThe reaction was left

Sources & evidence

ORD record
ord-5359824c7b014a8eb2734ff48cd601bf
Source dataset
uspto-grants-2016_03
Patent number
US09278987B2

Reaction notes

Loading…