Hydrochloric Acid → HCID 68726321, compound

HRID 1418045Notes

Reaction equation

HRID 1418045 reaction equation
COC1C(=O)C=[C:7]2[C@@H](N)C[CH2:13][C:14]3[C:19]([C:6]2=[CH:5]C=1)=[C:18]([O:20]C)C(OC)=C(OC)[CH:15]=3.C(O)(C(O)=O)C(O)C(O)=O.ON1C(=O)CCC1=O.Cl.[NH2:46][CH2:47][C:48]([NH2:50])=[O:49]>C(Cl)Cl.CCCCCC.CCOC(C)=O.CN(C=O)C.N(CC)(CC)CC>[CH3:7][C:6]1([CH3:5])[C:14]([CH3:13])([CH3:15])[CH:19]1[C:18]([NH:50][C:48](=[O:49])[CH2:47][NH2:46])=[O:20]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 340842,3-Dihydroxybutanedioic acid--7-amino-1,2,3,10-tetramethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one (1/1)HCID 69020GlycinamideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 68726321HCID 68726321, compoundYield 28%

Reagents, catalysts & solvents 5

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of TMCA (2.82 g, 20 mmole) in dry CH2Cl2 (150 ml) were added N-hydroxysuccinimide (2.3 g, 20 mmole) and DMAPE-carbodiimide.HCl (3.92 g, 20 mmole). The substance obtained was stirred for 15 hours at room temperature. To this mixture was added (CH3CH2)3N (4.5 ml), glycinamide.Hcl (2.2 g. 20 mmole) and dry DMF (100 ml), and stirred for 24 hours at room temperature. The solvents were stripped off under reduced pressure. The residue was purified by chromatography (SiO2, CHCl3 :MeOH 97:3) followed by successive crystallization from CH2Cl2 :hexane and EtOAc:hexane, to afford 1.1 g (5.6 mmole, 28%) of a white crystalline solid, m.p.: 176° C.

Workup

  1. customThe substance obtained
  2. customThe residue was purified by chromatography (SiO2, CHCl3 :MeOH 97:3)
  3. customfollowed by successive crystallization from CH2Cl2

Sources & evidence

ORD record
ord-494e3d8f7445414da7c3d185b3534fc1
Source dataset
uspto-grants-1999_03
Patent number
US05880157

Reaction notes

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