1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131736351, compound

HRID 1055427Notes

Reaction equation

HRID 1055427 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(OC(N(C)[C@@H](C)C(N[C@H]1C2(CCOCC2)OC2C=CC=CC=2N(C[C:35]2[C:44]([O:45][CH3:46])=[CH:43][CH:42]=[C:41]3[C:36]=2[CH:37]=[CH:38][C:39]([C:47](O)=[O:48])=[CH:40]3)C1=O)=O)=O)(C)(C)C.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:46][O:45][C:44]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[CH:40]=[C:39]([C:47]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:48])[CH:38]=[CH:37]2

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 131736350HCID 131736350, compound

Product 1

HCID 131736351HCID 131736351, compoundYield 255.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonamide (10.9 mg, 115 μmol, Eq: 1.25) was added to a mixture of 5-(((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-2-nap hthoic acid (59.4 mg, 91.7 μmol, Eq: 1.00), EDCI (22.0 mg, 115 μmol, Eq: 1.25) and DMAP (14.0 mg, 115 μmol, Eq: 1.25) in DCM (5 mL). After 2 h, the mixture was diluted with DCM, washed with 1 M HCl, brine, dried over Na2SO4 and concentrated to afford 5-((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-N-(methylsulfonyl)-2-naphthamide (65.4 mg) as a white foam which was used without purification.

Workup

  1. washwashed with 1 M HCl, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d335e5e28c5643cc95f03dba597d342b
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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