Reaction #220474

ord-9b25add83d814dcfb45e825517da4c1c

Reaction equation

O=C(O)C(O)C1CCCC1
cyclopentyl-α-hydroxyacetic acid
C[C@H](N)C(=O)C1(N)C(=O)N(CC2CC2)c2ccccc2N(CC2CC2)C1=O.Cl
3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride
C[C@H](N)C(=O)C1(N)C(=O)N(CC2CC2)c2ccccc2N(CC2CC2)C1=O.Cl
3-(L-Alaninyl)-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine Hydrochloride
→
C[C@H](NC(=O)C(O)C1CCCC1)C(=O)C1(N)C(=O)N(CC2CC2)c2ccccc2N(CC2CC2)C1=O
title compound
C[C@H](NC(=O)C(O)C1CCCC1)C(=O)C1(N)C(=O)N(CC2CC2)c2ccccc2N(CC2CC2)C1=O
3-[N′-(Cyclopentyl-α-hydroxyacetyl)-L-alaninyl]-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Reactants

O=C(O)C(O)C1CCCC1
cyclopentyl-α-hydroxyacetic acid
C[C@H](N)C(=O)C1(N)C(=O)N(CC2CC2)c2ccccc2N(CC2CC2)C1=O.Cl
3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride
C[C@H](N)C(=O)C1(N)C(=O)N(CC2CC2)c2ccccc2N(CC2CC2)C1=O.Cl
3-(L-Alaninyl)-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine Hydrochloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPurification
  2. 2
    Wash2000 eluting with CH2Cl2/EtOAc (1:1 gradient to 1:2) then flash chromatography eluting with 2:1 EtOAc/CH2Cl2

Procedure

Following General Procedure I above using cyclopentyl-α-hydroxyacetic acid (Example P) and 3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-U), the title compound was prepared as a white foam. Purification was by L.C. 2000 eluting with CH2Cl2/EtOAc (1:1 gradient to 1:2) then flash chromatography eluting with 2:1 EtOAc/CH2Cl2. Rf=0.47 and 0.37 (CH2Cl2/EtOAc, 1:2).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07390801B2uspto-grants-2008_06