(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclohexylpropanoic acid → HCID 178479446, compound

HRID 1450175Notes

Reaction equation

HRID 1450175 reaction equation
[NH2:1][C@@H:2]([C:10]([N:12]1[CH2:29][CH2:28][CH2:27][C@H:13]1[C:14]([NH:16][C@H:17]([CH:25]=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23])=[O:15])=[O:11])[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[ClH:30].O.N(C(OC(C)(C)C)=O)[C@@H](C(O)=O)CC1CCCCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[NH2:1][C@@H:2]([C:10]([N:12]1[CH2:29][CH2:28][CH2:27][C@H:13]1[C:14]([NH:16][C@H:17]([CH:25]=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:23])[NH2:24])=[O:15])=[O:11])[CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1.[ClH:30]

Participants

4

Reactant 3

HCID 2755927(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclohexylpropanoic acidHCID 21226445Aluminium lithium hydrideHCID 178479447HCID 178479447, compound

Product 1

HCID 178479446HCID 178479446, compound

Procedure

By methods substantially equivalent to those described in Example 1-A, 1-B, 1-C, 1-D, 1-H and 1-I, 2.14 g of NMI-D-Cha-Pro-Arg-H.HCl hydrate was prepared using Boc-D-Cha-OH in place of Boc-D-Phe-OH. Also, the tripeptide arginine lactam was reduced with LiAl(O-t-Bu)3H at -23° C. rather than LAH at -78° C.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-834849cc63eb4d0ba7f2029b583c82ff
Source dataset
uspto-grants-1997_02
Patent number
US05602101

Reaction notes

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