Water → HCID 76902876, compound

HRID 1404378Notes

Reaction equation

HRID 1404378 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[NH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])OC(C)(C)C.NCCNC1[CH2:31][CH:30]([CH2:32][C:33]([NH:35][C@H:36]([B:49]2[O:57]C3C(C)(C4CC(C3)C4(C)C)[O:50]2)[CH2:37][C:38]2[C:39](OC)=[C:40]([CH:44]=[CH:45][CH:46]=2)[C:41]([OH:43])=[O:42])=[O:34])[CH2:29]1.O>C(Cl)Cl.CN(C=O)C>[NH2:10][CH2:11][CH2:12][NH:8][C:1](=[O:2])[N:3]([CH:4]1[CH2:29][CH:30]([CH2:32][C:33]([NH:35][C@H:36]2[CH2:37][C:38]3[CH:46]=[CH:45][CH:44]=[C:40]([C:41]([OH:43])=[O:42])[C:39]=3[O:57][B:49]2[OH:50])=[O:34])[CH2:31]1)[CH2:7][CH2:6][NH:5][C:17]([NH:16][CH2:15][CH2:14][NH2:13])=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 187201N-BOC-ethylenediamineHCID 86722983HCID 86722983, compound

Product 1

HCID 76902876HCID 76902876, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 1,1′-Carbonyldiimidazole (180 mg) in DCM (5 mL) was added tert-butyl 2-aminoethylcarbamate (160 mg). The resultant reaction mixture was stirred at RT for 1 hr. A portion of this solution (1 mL) was then added to 3-((2R)-2-(2-(3-(2-aminoethylamino)cyclobutyl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoic acid from step 1 (20 mg) in DMF and TEA (2 eq) in a different flask. The reaction mixture was stirred overnight. Water was added and extracted with EtOAc. The combine organic phases were dried and concentrated in vacuo to afford the product which was used directly to next step.

Workup

  1. customThe resultant reaction mixture
  2. stirringThe reaction mixture was stirred overnight
  3. extractionextracted with EtOAc
  4. customThe combine organic phases were dried
  5. concentrationconcentrated in vacuo
  6. customto afford the product which

Sources & evidence

ORD record
ord-f68b52c6af81444e9562c6fd94d229ff
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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