L-Valine → HCID 178461042, compound

HRID 2273610Notes

Reaction equation

HRID 2273610 reaction equation
[CH2:1]([S:4]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[N:36]=[C:37]([C@@H:40]6[CH2:44][CH2:43][CH2:42][N:41]6C(OC(C)(C)C)=O)[NH:38][CH:39]=5)=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH3:52][CH:53]([C@H:55]([NH2:59])[C:56](O)=[O:57])[CH3:54].[C:60]([OH:66])(C(F)(F)F)=[O:61].[CH3:67]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:52][CH:53]([CH3:54])[C@H:55]([NH:59][C:60](=[O:61])[O:66][CH3:67])[C:56](=[O:57])[N:41]1[CH2:42][CH2:43][CH2:44][C@H:40]1[C:37]1[NH:38][CH:39]=[C:35]([C:32]2[CH:31]=[CH:30][C:29]([C:26]3[CH:25]=[CH:24][C:23]([C:21](=[O:22])[NH:20][C:17]4[CH:16]=[CH:15][C:14]([CH2:13][N:10]5[CH2:11][CH2:12][N:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:5])=[O:6])[CH2:8][CH2:9]5)=[CH:19][CH:18]=4)=[CH:28][CH:27]=3)=[CH:34][CH:33]=2)[N:36]=1

Participants

5

Reactant 4

HCID 6287L-ValineHCID 6422Trifluoroacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178461043HCID 178461043, compound

Product 1

HCID 178461042HCID 178461042, compound

Procedure

The title compound is prepared from (8) (above) and Moc-L-val-OH using the two-step TFA deprotection and HATU coupling sequence outlined above for the preparation of 5. Yield: 60.5 mg (81%, 2 steps). HPLC: tR1.82 min (method 1); tR 2.17 min, 97.6% purity (method 2). LC-MS m/z calcd for C41H51N7O6S ([M]+), 769. found, 770 ([M+H]+). 1H NMR (CDCl3, 50° C.): δ 0.88 (d, J=6.5 Hz, 6H), 1.06 (t, J=7.5 Hz, 3H), 1.84 (m, 2H), 1.90-2.42 (m, 4H), 2.56 (m, 4H), 2.87 (m, 2H), 3.05 (m, 1H), 3.32 (m, 4H), 3.57 (s, 2H), 3.62 (m, 1H), 3.70 (s, 3H), 3.82 (m, 1H), 4.32 (dd, J=9.0 Hz, 6.5 Hz, 1H), 5.26 (m, 1H), 5.32 (d, J=9.0 Hz, 1H), 7.24 (s, 1H), 7.32 (m, 2H), 7.61 (m, 4H), 7.67-7.87 (m, 4H), 7.93 (m, 2H).

Workup

  1. customoutlined above for the preparation of 5

Sources & evidence

ORD record
ord-90e291206f20471ead9c2e6478f17631
Source dataset
uspto-grants-2015_09
Patent number
US09125904B1

Reaction notes

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