Nalpha-t-butoxycarbonyl-D-valine p-nitrophenyl ester → HCID 178465160, compound

HRID 1763736Notes

Reaction equation

HRID 1763736 reaction equation
[ClH:1].C(NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(OCC1C=CC=CC=1)=O)C.Cl.Cl.[CH2:43]([NH:45][C:46](=[O:71])[C@@H:47]1[CH2:51][CH2:50][CH2:49][N:48]1[C:52](=[O:70])[C@H:53]([CH2:63][CH2:64][CH2:65][NH:66][C:67](=[NH:69])[NH2:68])[NH:54][C:55](=[O:62])[C@H:56]([CH2:58][CH:59]([CH3:61])[CH3:60])[NH2:57])[CH3:44].[N+](C1C=CC([O:81][C:82](=O)[C@@H:83]([CH:92]([CH3:94])[CH3:93])[NH:84][C:85]([O:87][C:88]([CH3:91])([CH3:90])[CH3:89])=[O:86])=CC=1)([O-])=O>CN(C)C=O>[ClH:1].[CH2:43]([NH:45][C:46](=[O:71])[C@@H:47]1[CH2:51][CH2:50][CH2:49][N:48]1[C:52](=[O:70])[C@H:53]([CH2:63][CH2:64][CH2:65][NH:66][C:67](=[NH:68])[NH2:69])[NH:54][C:55](=[O:62])[C@H:56]([CH2:58][CH:59]([CH3:60])[CH3:61])[NH:57][C:82](=[O:81])[C@@H:83]([CH:92]([CH3:93])[CH3:94])[NH:84][C:85]([O:87][C:88]([CH3:89])([CH3:90])[CH3:91])=[O:86])[CH3:44]

Participants

5

Reactant 3

HCID 22804944Nalpha-t-butoxycarbonyl-D-valine p-nitrophenyl esterHCID 178465162HCID 178465162, compoundHCID 178465165HCID 178465165, compound

Product 1

HCID 178465160HCID 178465160, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Nα -t-butoxycarbonyl-D-valyl-L-leucyl-L-arginyl-L-proline N-ethylamide hydrochloride is prepared from 3.8 g., 6.5 mmol, of Nα -benzyloxycarbonyl-L-leucyl-L-arginyl-L-proline N-ethylamide hydrochloride by de-protection by the hydrogenation procedure as described in Example 2, to yield 2.9 g., 6.5 mmol, of L-leucyl-L-arginyl-L-proline N-ethylamide dihydrochloride as a glassy solid. This material is dissolved in 25 ml. of dimethylformamide and treated with 2.2 g., 6.5 mmol, of Nα -t-butoxycarbonyl-D-valine p-nitrophenyl ester. The reaction is held at room temperature for four days and is then evaporated to dryness under reduced pressure. The residue is dissolved in 10 ml. of methanol and the product precipitated by the addition of 500 ml. of anhydrous ether. The solid product is purified by chromatography over silica gel with toluene-methanol (70:30); 1.1 g.; [α]D23 -53.5° (c 1.0, methanol).

Workup

  1. customto yield 2.9 g
  2. dissolutionThis material is dissolved in 25 ml
  3. customis then evaporated to dryness under reduced pressure
  4. dissolutionThe residue is dissolved in 10 ml
  5. customof methanol and the product precipitated by the addition of 500 ml
  6. customThe solid product is purified by chromatography over silica gel with toluene-methanol (70:30)

Sources & evidence

ORD record
ord-f257323c82ce4b26a3b9367a5576e8cb
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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