Diisopropylethylamine → HCID 57661612, compound

HRID 2400317Notes

Reaction equation

HRID 2400317 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.CCN(C(C)C)C(C)C.[NH2:57][C@H:58]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[CH2:59][CH2:60][C:61](=[O:63])[OH:62]>C1COCC1.CN1C(=O)CCC1>[C:67]([O:66][C:64](=[O:65])[C@@H:58]([NH:57][C:25](=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:10]1[S:9][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:12][CH:11]=1)[CH2:59][CH2:60][C:61]([OH:63])=[O:62])([CH3:70])([CH3:68])[CH3:69]

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamateHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 57661609HCID 57661609, compound

Product 1

HCID 57661612HCID 57661612, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-(12-carboxydodecyl)-thiophene-2-carboxylic acid tert-butyl ester (31 mg, 0.0 78 mmol) was treated with TSTU (28.2 mg, 0.094 mmol) and DIPEA (0.016 mL, 0.094 mmol) in THF (1.3 mL) for 2½ hours at room temperature under nitrogen. The solvent was removed in vacuo and the mixture added NMP (1 mL) and H-Glu-OtBu (31.3 mg, 0.154 mmol) and DIPEA (0.027 mL). The mixture was stirred overnight at room temperature. The mixture was separated between diethyl ether (10 mL) and 10% aqueous NaHSO4 (2×10 mL) and the organic phase isolated and solvent removed in vacuo to give the crude (S)-2-[13-(5-tert-Butoxycarbonylthiophen-2-yl)-tridecanoylamino]-pentanedioic acid 1-tert-butyl ester which was subsequently in the next step without any further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe mixture was separated between diethyl ether (10 mL) and 10% aqueous NaHSO4 (2×10 mL)
  3. customthe organic phase isolated
  4. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-4494aa9e81334d518bd1f9c27e0d0b96
Source dataset
uspto-grants-2014_08
Patent number
US08796205B2

Reaction notes

Loading…