Diisopropylethylamine → HCID 86612926, compound

HRID 460414Notes

Reaction equation

HRID 460414 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH:9]1[CH2:13][CH:12]([OH:14])[CH:11]([OH:15])[CH2:10]1.CCN(C(C)C)C(C)C.[N:25]1([C:31]([NH:33][C@@H:34]([CH2:38][S:39]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)(=[O:41])=[O:40])[C:35](O)=[O:36])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:15][CH:11]1[CH:12]([OH:14])[CH2:13][CH:9]([NH:8][C:35]([C@@H:34]([NH:33][C:31]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:32])[CH2:38][S:39]([CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)(=[O:41])=[O:40])=[O:36])[CH2:10]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11439693(R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acidHCID 86612927HCID 86612927, compound

Product 1

HCID 86612926HCID 86612926, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-cyclopentane-1,2-diol; compound with trifluoroacetic acid (745 mg, 3.23 mmol) in DMF (15 ml) was treated with DIPEA (1.12 ml, 6.4 mmol) and the mixture was stirred for 5 minutes at room temperature. Then (R)-2-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (1.15 g, 3.23 mmol) was added followed by HATU (1.23 g, 3.24 mmol). This mixture was stirred at room temperature overnight and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate and then with a mixture of ethyl acetate and methanol to give morpholine-4-carboxylic acid [(R)-1-(3,4-dihydroxy-cyclopentylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide as a brown solid (680 mg). LC/MS: RT=2.64 min. (215 and 254 nM), MH+=456.

Workup

  1. stirringThis mixture was stirred at room temperature overnight
  2. customevaporated
  3. additionwith a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-b15e9185bd194491af69548d2bd8388f
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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