N-((Phenylmethoxy)carbonyl)-D-phenylalanine 4-nitrophenyl ester → HCID 178445953、化合物

HRID 2083827ノート

反応式

HRID 2083827 の反応式
[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

参加物

5

反応物 3

HCID 12448569N-((Phenylmethoxy)carbonyl)-D-phenylalanine 4-nitrophenyl esterHCID 178446031HCID 178446031、化合物HCID 178447115HCID 178447115、化合物

生成物 1

HCID 178445953HCID 178445953、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d328138a222f469790617e4f94760f62
出典データセット
uspto-grants-1978_04
特許番号
US04086219

反応ノート

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