Triethylamine → HCID 131725285, compound

HRID 890920Notes

Reaction equation

HRID 890920 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.FC1C(O)=C(F)C(F)=C(F)C=1F.C(N=C=NC(C)C)(C)C.Cl.[OH:33][CH:34]1[O:42][C@H:41]([CH2:43][OH:44])[C@@H:39]([OH:40])[C@H:37]([OH:38])[C@H:35]1[NH2:36].CCN(CC)CC>CN(C=O)C.CN(C=O)C.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:34]2([O:42][C@H:41]([CH2:43][OH:44])[C@@H:39]([OH:40])[C@H:37]([OH:38])[C@H:35]2[NH2:36])[OH:33])=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 120854-Iodobenzoic acidHCID 12734DiisopropylcarbodiimideHCID 13041PentafluorophenolHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

Product 1

HCID 131725285HCID 131725285, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

To a solution of 4-iodobenzoic acid (1 mmol) in DMF (2 mL) was added pentafluorophenol (2 mmol) and diisopropylcarbodiimide (1.2 mmol). The solution was stirred at room temperature for 6 hours and then added to a solution of glucosamine hydrochloride (1 mmol) and NEt3 (2 mmol) in DMF/H2O (1 mL, 1:10 v/v). The reaction was stirred for 16 hours and then crystallized from hot water to yield 4-iodobenzoyl glucosamine, compound TP010. The structure of TP010 is shown below (R is I).

Workup

  1. stirringThe reaction was stirred for 16 hours
  2. customcrystallized from hot water

Sources & evidence

ORD record
ord-f4523c1ac91d48d39ecce5bc0be97046
Source dataset
uspto-grants-2006_02
Patent number
US07001888B2

Reaction notes

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