Tetrahydrofuran → HCID 87253071, compound

HRID 535285Notes

Reaction equation

HRID 535285 reaction equation
C([O:5][C:6](=[O:49])[CH:7]([NH:13][C:14](=[O:48])[CH2:15][CH2:16][C:17](=[O:47])[NH:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])(C)(C)C.CCN([CH:56]([CH3:58])[CH3:57])C(C)C.[B-](F)(F)(F)F.CN(C(O[N:72]1[C:77](=[O:78])[CH2:76][CH2:75][C:73]1=[O:74])=[N+](C)C)C.[CH2:79]1COCC1>CN(C=O)C>[O:74]=[C:73]1[CH2:75][CH2:76][C:77](=[O:78])[N:72]1[O:5][C:6](=[O:49])[CH:7]([NH:13][C:14](=[O:48])[CH2:15][CH2:16][C:17](=[O:47])[NH:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:8][CH2:9][C:10]([O:12][C:56]([CH3:58])([CH3:79])[CH3:57])=[O:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 72302912HCID 72302912, compound

Product 1

HCID 87253071HCID 87253071, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[3-(3-{4-[3-(7-tert-butoxycarbonylheptanoylamino)propoxy]butoxy}-propylcarbamoyl)-propionylamino]pentanedioic acid 1-tert-butyl ester (1.5 g, 2.14 mmol) was dissolved in THF (20 mL), pH was adjusted to 8.5 with DIPEA (0.9 mL), TSTU (0.83 g, 2.77 mmol) was added in DMF (5 mL). The mixture was stirred under nitrogen overnight, subsequent evaporation and extraction between EtAc and HCl as described above resulted in 1.75 g crude product.

Workup

  1. customsubsequent evaporation and extraction between EtAc and HCl

Sources & evidence

ORD record
ord-5f248fcecc4541ddbf95087efae37e63
Source dataset
uspto-grants-2014_10
Patent number
US08859493B2

Reaction notes

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