N-((Phenylmethoxy)carbonyl)-D-phenylalanine 4-nitrophenyl ester → HCID 178445953, compound

HRID 2083827Notes

Reaction equation

HRID 2083827 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:8]([NH:10][C@H:11]([C:19]([N:21]1[CH2:32][CH2:31][CH2:30][C@H:22]1[C:23]([NH:25][CH2:26][C:27]([NH2:29])=[O:28])=[O:24])=[O:20])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:18])[NH2:17])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].Cl.C(ON[C@H](C(N[C@H](C(N1CCC[C@H]1C(NCC(N)=O)=O)=O)CCCNC(=N)N)=O)C(=C=O)C(C)C)C1C=CC=CC=1.[N+](C1C=CC([O:84][C:85](=O)[C@@H:86]([CH2:98][C:99]2[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=2)[NH:87][C:88]([O:90][CH2:91][C:92]2[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=2)=[O:89])=CC=1)([O-])=O>CN(C)C=O>[ClH:1].[CH2:91]([O:90][C:88]([NH:87][C@@H:86]([C:85]([NH:2][C@H:3]([C:8]([NH:10][C@H:11]([C:19]([N:21]1[CH2:32][CH2:31][CH2:30][C@H:22]1[C:23]([NH:25][CH2:26][C:27]([NH2:29])=[O:28])=[O:24])=[O:20])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:17])[NH2:18])=[O:9])[CH2:4][CH:5]([CH3:6])[CH3:7])=[O:84])[CH2:98][C:99]1[CH:100]=[CH:101][CH:102]=[CH:103][CH:104]=1)=[O:89])[C:92]1[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=1

Participants

5

Reactant 3

HCID 12448569N-((Phenylmethoxy)carbonyl)-D-phenylalanine 4-nitrophenyl esterHCID 178446031HCID 178446031, compoundHCID 178447115HCID 178447115, compound

Product 1

HCID 178445953HCID 178445953, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The L-leucyl-L-arginyl-L-prolyl-glycinamide hydrochloride obtained from de-protection of 6.43 g. of Nα -benzyloxy-carbonyl-L-leucyl-L-arginyl-L-prolyl-glycinamide hydrochloride, 4.3 g. of Nα -benzyloxycarbonyl-D-phenylalanine p-nitrophenyl ester (prepared as for the L-isomer, J. Org. Chem. 27, 3409 (1962)) and 30 ml. of dimethylformamide is stirred until solution is complete. The solution is allowed to stand at 25° C. for 24 hours, filtered from a small amount of fine solid and again allowed to stand at 25° C. for 24 hours. The solution is evaporated to dryness at 40° C. under reduced pressure. The residue is dissolved in methanol (40 ml.) and ethyl acetate (30 ml.) and dropped into 300 ml. of stirred dry diethyl ether. The granular solid which precipitates is separated by decanting and the precipitation is repeated. The solid is separated and dried at 45° C. under reduced pressure to give 6.5 g. of product suitable for use but showing by ultraviolet absorption 0.37% of p-nitrophenol; [α]D23 -54.6° (c 1.0, methanol); ultraviolet in methanol λmax 257 E11 5.8.

Workup

  1. filtrationfiltered from a small amount of fine solid
  2. waitto stand at 25° C. for 24 hours
  3. customThe solution is evaporated to dryness at 40° C. under reduced pressure
  4. dissolutionThe residue is dissolved in methanol (40 ml.)
  5. additionethyl acetate (30 ml.) and dropped into 300 ml
  6. customThe granular solid which precipitates
  7. customis separated
  8. customby decanting
  9. customthe precipitation
  10. customThe solid is separated
  11. customdried at 45° C. under reduced pressure
  12. customto give 6.5 g
  13. customof product suitable for use but showing by ultraviolet absorption 0.37% of p-nitrophenol

Sources & evidence

ORD record
ord-d328138a222f469790617e4f94760f62
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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