(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid → 5-Methylpyrrolidine-2-carboxylic acid

HRID 590675Notes

Reaction equation

HRID 590675 reaction equation
COC(N[C@@H](C(C)C)C(O)=O)=O.[CH3:13][C@@H:14]1[CH2:19][CH:18]([C@H:20]([NH:24]C(OC)=O)[C:21]([OH:23])=[O:22])C[C@@H](C)O1>>[CH3:13][CH:14]1[NH:24][CH:20]([C:21]([OH:23])=[O:22])[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 66746681(S)-2-((2R,6R)-2,6-Dimethyltetrahydro-2H-pyran-4-yl)-2-((methoxycarbonyl)amino)acetic acid

Product 1

HCID 4088125-Methylpyrrolidine-2-carboxylic acid

Procedure

(2S,5S)-1-(S)-2-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-(methoxycarbonylamino)acetyl)-5-methylpyrrolidine-2-carboxylic acid was synthesized in a similar manner as Intermediate 4 substituting (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid with (S)-2-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-(methoxycarbonylamino)acetic acid. 1H NMR (400 MHz, Chloroform-d) δ 5.33-5.16 (m, 1H), 4.70-4.59 (m, 1H), 4.54 (t, 1H), 4.34-4.19 (m, 2H), 4.12 (q, 1H), 3.78-3.70 (m, 1H), 3.67 (s, 3H), 2.37-2.17 (m, 3H), 2.15-2.07 (m, 1H), 2.04 (s, 1H), 1.84-1.73 (m, 1H), 1.82-1.43 (m, 3H), 1.32 (d, 3H), 1.26 (d, 4H), 1.11 (d, 3H), 0.96 (q, 1H). LCMS-ESI+ calc'd for C17H29N2O6: 357.19. Found: 357.08.

Sources & evidence

ORD record
ord-4f3f9f9637a74ce4a648df677edb3713
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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