Dicyclohexylcarbodiimide → HCID 54311645, compound

HRID 442236Notes

Reaction equation

HRID 442236 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([N:22]1[CH2:68][CH2:67][CH2:66][C@H:23]1[C:24]([N:26]1[CH2:65][CH2:64][CH2:63][C@H:27]1[C:28]([NH:30][C@H:31]([C:47]([NH:49][C@H:50]([C:60]([OH:62])=[O:61])[CH2:51][O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:48])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:35][CH:34]=1)=[O:29])=[O:25])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:69](OC(N[C@H](C(O)=O)COCC1C=CC=CC=1)=O)(C)(C)C.C(OC(N[C@H](C(O)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1)=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1.C(OC(N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)(C)(C)C>CO>[CH3:69][O:61][C:60](=[O:62])[C@H:50]([CH2:51][O:52][CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[NH:49][C:47](=[O:48])[C@H:31]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:35][CH:34]=1)[NH:30][C:28](=[O:29])[C@@H:27]1[CH2:63][CH2:64][CH2:65][N:26]1[C:24](=[O:25])[C@@H:23]1[CH2:66][CH2:67][CH2:68][N:22]1[C:20](=[O:21])[C@H:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

7

Reactant 5

HCID 10868Dicyclohexylcarbodiimide4×HCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 54543957HCID 54543957, compound

Product 1

HCID 54311645HCID 54311645, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nα -t-Butoxycarbonyl-L-tryptophyl-L-prolyl-L-prolyl-O-benzyl-L-tyrosyl-O-benzyl-L-serine resin, 20 g., (24 mmol) is converted to the methyl ester by the procedure of Example 1 yielding the above named product in the form of a glass [α]D23 -68° (c. 1.05 in methanol). The above resin is prepared according to the procedure of Example 1using Nα -t-butoxycarbonyl-O-benzyl-L-serine resin which is successively reacted with 1) 8.9 g. (24 mmol) of Nα -t-butoxycarbonyl-O-benzyl-L-tyrosine and 5 g. (24.2 mmol) of dicyclohexylcarbodiimide, 2) 5.0 g. (23.2 mmol) of Nα -t-butoxycarbonyl-L-proline and 5.0 g, of dicyclohexylcarbodiimide, 3) 5 g. (23.2 mmol) of Nα -t-butoxycarbonyl-L-proline and 5.0 g. of dicyclohexylcarbodiimide and 4) 7.30 g. (24 mmol) of Nα -t-butoxycarbonyl-L-tryptophane and 5 g. (23.2 mmol) dicyclohexylcarbodiimide.

Workup

  1. customThe above resin is prepared
  2. customis successively reacted with 1) 8.9 g

Sources & evidence

ORD record
ord-d7e1355655894a92b219f2d829c26232
Source dataset
uspto-grants-1977_08
Patent number
US04043993

Reaction notes

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