Diisopropylethylamine → HCID 69347500, compound

HRID 1793262Notes

Reaction equation

HRID 1793262 reaction equation
[NH2:1][CH2:2][C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17].[CH:20]1[C:32]2[CH:31]([CH2:33][O:34][C:35]([NH:37][C@H:38]([C:43](O)=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:36])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.C(N(C(C)C)CC)(C)C.C(NCC(NC[C@]1(CO)O[C@@H](N2C=C(C)C(=O)NC2=O)C[C@@H]1O)=O)(=O)C>CN(C=O)C>[CH:29]1[C:30]2[CH:31]([CH2:33][O:34][C:35]([NH:37][C@H:38]([C:43]([NH:1][CH2:2][C@:3]3([CH2:18][OH:19])[O:7][C@@H:6]([N:8]4[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]4=[O:10])[CH2:5][C@@H:4]3[OH:17])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:36])[C:32]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]=2[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 1549133Fmoc-leucineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 10292555HCID 10292555, compoundHCID 22881721HCID 22881721, compound

Product 1

HCID 69347500HCID 69347500, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-C-(Aminomethyl)thymidine (4) (0.025 g, 0.1 mmol), N-(9-fluorenylmethyloxycarbonyl)leucine (0.071 g, 0.2 mmol), TSTU (0.09 g, 0.3 mmol) and diisopropylethylamine (0.065 g, 0.5 mmol, 0.087 mL) were combined in DMF (1 mL) according to the procedure used to prepare compound (19). The title compound (20) was obtained as an amorphous solid (0.056 g). δH(300 MHz, CD3OD) 7.86–7.37(8H, m, Fmoc), 7.74(1H, s, H-6), 6.24(1H, dd, H-1′), 4.56(1H, dd, H-3′), 3.68(2H, 2d, H-5′), 3.40(2H, 2d, 4′-C—CH2), 2.37(2H, m, H-2′), 1.70(3H, m, leucyl CH, CH2), 1.66(3H, s, 5-CH3), 1.05(3H, d, leucyl CH3), 1.02(3H, d, leucyl CH3); ES +ve m/z 607(M+H)+, 629(M+Na)+.

Sources & evidence

ORD record
ord-c9949be2671b4e299f745542bda2d702
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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