HCID 86759042, compound → HCID 178462168, compound

HRID 1355596Notes

Reaction equation

HRID 1355596 reaction equation
[CH2:1]([S:8]([NH:11][C@@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C@H:19]([C:21]([OH:23])=O)[CH3:20].C(OC([N:31]([C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH-:40])=[CH:37][CH:36]=1)[C:32]([NH2:34])=[NH:33])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([S:8]([NH:11][C@@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])(=[O:9])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH:31]([C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:21](=[O:23])[C@H:19]([CH3:20])[NH2:18])=[CH:37][CH:36]=1)[C:32]([NH2:34])=[NH:33]

Participants

4

Reactant 2

HCID 86759042HCID 86759042, compoundHCID 86759043HCID 86759043, compound

Product 1

HCID 178462168HCID 178462168, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution benzylsulfonyl-D-serine-L-alanine-(4-(N-tert-butoxycarbonylguanidino) benzylamide (7-5) (9.0 mg, 0.016 mmol), in a mixture of CH2Cl2/TFA (1:1, 600 μl) was stirred at room temperature for 90 minutes. The solvent was removed in vacuo to give a transparent oil. HPLC purification (CH3CN, H2O, 0.1% TFA) gave a fluffy white solid as the title compound (5.0 mg, 66%), MS (electrospray) 477 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a transparent oil
  3. customHPLC purification (CH3CN, H2O, 0.1% TFA)

Sources & evidence

ORD record
ord-cca3ae7f413941a2b6f80144bb536d0d
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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