Diisopropylethylamine → 9H-fluoren-9-ylmethyl 11-[(3,3-diethoxypropyl)amino]-11-oxoundecyl-carbamate

HRID 25700Notes

Reaction equation

HRID 25700 reaction equation
[C:1](C(CCCCCCCCCN)C(O)=O)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[OH:32][C:33]1[C:41]2N=NN[C:37]=2[CH:36]=[CH:35][CH:34]=1.Cl.CN(C)[CH2:45][CH2:46][CH2:47][N:48]=C=NCC.[NH2:54][CH2:55][CH2:56][CH:57]([O:61][CH2:62][CH3:63])[O:58][CH2:59][CH3:60].[CH:64](N(CC)C(C)C)(C)[CH3:65]>O1CCCC1>[CH2:59]([O:58][CH:57]([O:61][CH2:62][CH3:63])[CH2:56][CH2:55][NH:54][C:33](=[O:32])[CH2:41][CH2:37][CH2:36][CH2:35][CH2:34][CH2:64][CH2:65][CH2:45][CH2:46][CH2:47][NH:48][C:1](=[O:2])[O:3][CH2:4][CH:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:60]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5475896111-amino-2-(9H-fluoren-9-ylmethoxycarbonyl)undecanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 207598659H-fluoren-9-ylmethyl 11-[(3,3-diethoxypropyl)amino]-11-oxoundecyl-carbamateYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 13, Fmoc-11-aminoundecanoic acid (2 g, 4.7 mmol), hydroxybenzotriazole (639 mg, 4.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (906 mg, 4.7 mmol), 1-amino-3,3-diethoxypropane (662 gm, 4.5 mmol) and N,N-diisopropylethylamine (0.834 ml, 4.7 mmol) were reacted in anhydrous tetrahydrofuran (30 ml) at room temperature for 16 hours. Purification by chromatography (flash column, silica gel, 50-80% ethyl acetate in hexanes then 10% methanol in methylene chloride) provided 9H-fluoren-9-ylmethyl 11-[(3,3-diethoxypropyl)amino]-11-oxoundecyl-carbamate (560 mg, 23%) as a white solid.

Workup

  1. customPurification by chromatography (flash column, silica gel, 50-80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1f2bee5318ed4281a52295de70ec8997
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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