Benzoic Acid → HCID 67995097, compound

HRID 2042960Notes

Reaction equation

HRID 2042960 reaction equation
Cl.[NH2:2][CH2:3][C:4](=[O:52])[CH2:5][C:6]1[CH:11]=[C:10]([C@H:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[O:13]2)[CH:9]=[CH:8][C:7]=1[Cl:51].[C:53](O)(=[O:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl>CN(C=O)C>[Cl:51][C:7]1[CH:8]=[CH:9][C:10]([C@H:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[O:13]2)=[CH:11][C:6]=1[CH2:5][C:4](=[O:52])[CH2:3][NH:2][C:53](=[O:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

8

Reactant 6

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67995269HCID 67995269, compound

Product 1

HCID 67995097HCID 67995097, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-amino-3-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)propan-2-one hydrochloride (1.75 g, 2.35 mmol), benzoic acid (430 mg, 3.53 mmol), EDCI (901 mg, 4.70 mmol) and HOBt (699 mg, 5.17 mmol) in DMF (15 mL) was added NMM (1.29 mL, 11.8 mmol). The resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 1.0 M HCl solution, and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography to provide the titled amide intermediate (980 mg, 51%). MH+706.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. customevaporated under vacuum
  4. customThe residue was further purified by silica column chromatography

Sources & evidence

ORD record
ord-ea24ea4e81df435bbc9ee55fbb590ffd
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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