Diisopropylethylamine → 5-{9-[(s)-1-Tert-butoxycarbonyl-3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-propylcarbamoyl]-nonyloxy}-isophthalic acid di-tert-butyl ester

HRID 1022420Notes

Reaction equation

HRID 1022420 reaction equation
[C:1]([O:5][C:6](=[O:46])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:45])[NH:31][C@H:32]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:60]1[C:65](=[O:66])[CH2:64][CH2:63][C:61]1=[O:62])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[C:13]([O:12][C:10](=[O:11])[C:9]1[CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:45])[NH:31][C@H:32]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:33][CH2:34][C:35]([O:37][N:60]2[C:65](=[O:66])[CH2:64][CH2:63][C:61]2=[O:62])=[O:36])[CH:19]=[C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:46])[CH:8]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate2×HCID 68443966HCID 68443966, compound

Product 1

HCID 874559205-{9-[(s)-1-Tert-butoxycarbonyl-3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-propylcarbamoyl]-nonyloxy}-isophthalic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[9-((S)-1-tert-Butoxycarbonyl-3-carboxy-propylcarbamoyl)-nonyloxy]-isophthalic acid di-tert-butyl ester (70 mg, 0.11 mmol) was dissolved in dry THF (1 ml). TSTU (40 mg, 0.13 mmol) and DIPEA (0.05 ml) was added. The mixture was stirred at room temperature under nitrogen over the weekend. The mixture was concentrated. The residue was redissolved in EtOAc and filtered. The filtrate was washed with 0.1N HCl (2×), washed with brine (1×), dried (Na2SO4) and concentrated to give a clear syrup. There was still starting material present and the TSTU-treatment was repeated followed by work up to give the title compound as a clear syrup.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was redissolved in EtOAc
  3. filtrationfiltered
  4. washThe filtrate was washed with 0.1N HCl (2×)
  5. washwashed with brine (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give a clear syrup

Sources & evidence

ORD record
ord-5f55972c60ad40db876a1df4a68ce6b1
Source dataset
uspto-grants-2014_05
Patent number
US08722620B2

Reaction notes

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