Diisopropylethylamine → 2-(19-tert-Butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl)ester

HRID 1748237Notes

Reaction equation

HRID 1748237 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH:7]([NH:13][C:14](=[O:40])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:64]1[C:69](=[O:70])[CH2:68][CH2:67][C:65]1=[O:66])=[N+](C)C)C>C1COCC1.C(#N)C>[O:66]=[C:65]1[CH2:67][CH2:68][C:69](=[O:70])[N:64]1[O:11][C:10](=[O:12])[CH2:9][CH2:8][CH:7]([NH:13][C:14](=[O:40])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:41]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 87275405HCID 87275405, compound

Product 1

HCID 866445302-(19-tert-Butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl)esterYield 81.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-(19-tert-Butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester (6.52 g, 11.17 mmol) was dissolved in THF (100 mL), DIPEA (2.14 mL) was added followed by a solution of TSTU (3.70 g, 12.29 mmol) in acetonitrile (25 mL). The mixture was stirred overnight at RT, then it was evaporated resulting in a brownish residue which was recrystallised from acetonitrile. After cooling overnight at 5° C. a powder was formed. This was dissolved in THF and dried with MgSO4, filtered and evaporated to dryness to afford 6.17 g (81%) of the title compound.

Workup

  1. customit was evaporated
  2. customresulting in a brownish residue which
  3. customwas recrystallised from acetonitrile
  4. temperatureAfter cooling overnight at 5° C. a powder
  5. customwas formed
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-46e62a2b9bd64f788999ebb85239e690
Source dataset
uspto-grants-2015_10
Patent number
US09150633B2

Reaction notes

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