Hydrochloric Acid → HCID 89486502, compound

HRID 2042959Notes

Reaction equation

HRID 2042959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[CH:23][N:24]=1.[NH:30]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:31]([C:36](O)=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:42]([O:41][C:39]([NH:30][C@@H:31]([C@@H:32]([CH3:33])[CH2:34][CH3:35])[C:36]([O:18][CH2:17][C@@H:10]1[C@@H:11]([OH:16])[C@H:12]([OH:15])[C@@H:13]([OH:14])[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:19][C:20]3[S:21][C:22]([C:25]4[O:26][CH:27]=[CH:28][CH:29]=4)=[CH:23][N:24]=3)[CH:4]=2)[O:9]1)=[O:37])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 51003384HCID 51003384, compound

Product 1

HCID 89486502HCID 89486502, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of parent compound 89 (438 mg, 1.0 mmol), N-Boc-Ile (463 mg, 2.0 mmol), EDCI (384 mg, 2.0 mmol) and DMAP (162 mg, 1.3 mmol) in DMF (0.9 mL) was stirred at room temperature for 15 h. 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 intermediate (157 mg, 24%). MH+651.

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-46a36613c22e492dbe708e3c56ae4697
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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