1-Hydroxybenzotriazole → 1-[(11-Carboxyundecanoyl)amino]-1-deoxy-d-glucitol

HRID 1831863Notes

Reaction equation

HRID 1831863 reaction equation
[C:1]([O:16]CC1C=CC=CC=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O-:14])=[O:13].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:46][CH2:47][C@@H:48]([C@H:50]([C@@H:52]([C@@H:54]([CH2:56][OH:57])[OH:55])[OH:53])[OH:51])[OH:49]>CN(C=O)C.O>[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([NH:46][CH2:47][C@@H:48]([C@H:50]([C@@H:52]([C@@H:54]([CH2:56][OH:57])[OH:55])[OH:53])[OH:51])[OH:49])=[O:16])([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 452501GlucamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2205272712-(Benzyloxy)-12-oxododecanoate

Product 1

HCID 116397761-[(11-Carboxyundecanoyl)amino]-1-deoxy-d-glucitolYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Monobenzyl dodecanedioate (530 mg, 1.7 mmol) was dissolved in 10 mL of DMF, to which EDC (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride) (325 mg, 1.7 mmol) and HOBt (1-hydroxybenzotriazole) (230 mg, 1.7 mmol) were added. The mixture was stirred at room temperature for one hour and then D-glucamine (380 mg, 1.9 mmol) was added. The mixture was stirred at room temperature overnight, poured into 50 mL water, agitated and filtered to give the desired amide, of formula IIa in 95% yield. NMR (DMSO-D-6)7.70(brm, 1H), 7.30(m, 5H), 5.07(s, 2H), 4.73(d, 1H, J=4.5 Hz), 4.44(d, 1H, J=5.4 Hz), 4.36(d, 1H, J=6.0 Hz), 4.32 (t, 1H, J=5.7 Hz), 4.24(d, 1H, J=6.6 Hz), 3.58–3.52(m, 3H), 3.50–3.40(m, 3H), 3.21(m, 1H), 3.00(m, 1H), 2.33(t, 2H, J=7.2 Hz), 2.05(t, 2H, J=7.2 Hz), 1.50(m, 4H), 1.22(m, 12H).

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature overnight
  3. stirringagitated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-56352a26ed954bcdad031626dd57bf66
Source dataset
uspto-grants-2006_06
Patent number
US07067689B1

Reaction notes

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