Acetic Acid → HCID 11635202, compound

HRID 2219896Notes

Reaction equation

HRID 2219896 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([N:13]1[CH:17]=[C:16]([CH2:18][C@@H:19]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:20]([OH:22])=[O:21])[N:15]=[N:14]1)[CH2:8][CH2:7][CH2:6]2)=O.CC(O)=O.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH3:33][C:30]1[CH:29]=[CH:28][C:27]([S:24]([NH:23][C@H:19]([CH2:18][C:16]2[N:15]=[N:14][N:13]([C@H:9]3[C:10]4[C:5](=[CH:4][C:3]([CH2:1][N:38]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]5)=[CH:12][CH:11]=4)[CH2:6][CH2:7][CH2:8]3)[CH:17]=2)[C:20]([OH:22])=[O:21])(=[O:25])=[O:26])=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 8082PiperidineHCID 86623612HCID 86623612, compound

Product 1

HCID 11635202HCID 11635202, compound

Procedure

(2R)-3-(1-(6-Formyl-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)-2-(4-methylphenylsulfonamido)-propanoic acid (85.8 μM, 1 eq) piperidine (3 eq) and HOAc (3 eq) were heated to 40° C. for 3 d. Additional portions of piperidine (3 eq) and HOAc (3 eq) were then added. After 2 h, MP-BH4 was added and the reaction mixture was allowed to stir for 3 days. The reaction mixture was concentrated and was purified using reverse phase conditions C18 (0-100% acetonitrile/water) to afford the title compound. MS (m/z): 538.2 (m+H).

Workup

  1. additionMP-BH4 was added
  2. concentrationThe reaction mixture was concentrated
  3. customwas purified

Sources & evidence

ORD record
ord-014964e82dff4c1db3e94d3f2f01a23f
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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