HCID 22312692, compound → HCID 22984269, compound

HRID 411399Notes

Reaction equation

HRID 411399 reaction equation
[CH:1]1([CH:6]([OH:10])[C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.N[C@H](C([C:17]1([NH2:40])[C:23](=[O:24])[N:22]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:21]2[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=2[N:19]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:18]1=[O:39])=O)C>>[CH:1]1([CH:6]([OH:10])[C:7]([NH:40][C@H:17]([C:23]([NH:40][CH:17]2[C:18](=[O:39])[N:19]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:20]3[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=3[N:22]([CH2:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:23]2=[O:24])=[O:24])[CH3:18])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 22312692HCID 22312692, compoundHCID 69034686HCID 69034686, compound

Product 1

HCID 22984269HCID 22984269, compound

Procedure

Following General Procedure I above using cyclopentyl-α-hydroxyacetic acid (Example P) and 3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-(2,2-dimethylpropyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-V), the title compound was prepared as a white solid (melting point=119-129° C.). Purification was by flash chromatography eluting with CH2Cl2/EtOAc (1:1 gradient to 2:3). Rf=0.42 and 0.28 (CH2Cl2/EtOAc, C29H44N4O5 (MW 528.70); mass spectroscopy (MH+) 529.2 (MH−) 527.4. Anal. Calcd. for C29H44N4O5: C, 65.88; H, 8.39; N, 10.60. Found: C, 65.56; H, 8.03; N, 10.35.

Workup

  1. customPurification
  2. washeluting with CH2Cl2/EtOAc (1:1 gradient to 2:3)

Sources & evidence

ORD record
ord-de6d5a8703a14fafa602c1a100e51ebb
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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