(2s)-2-[(2-Amino-1,3-Thiazol-4-Yl)methyl]-N~1~-[(1s,2r,3r)-1-(Cyclohexylmethyl)-2,3-Dihydroxy-5-Methylhexyl]-N~4~-[2-(Dimethylamino)-2-Oxoethyl]-N~4~-[(1s)-1-Phenylethyl]butanediamide → 2(R)-(cyclopropylmethyl)butanedioic acid

HRID 1737118Notes

Reaction equation

C([O:5][C:6](=[O:32])[CH2:7][C@@H:8]([CH2:28][CH:29]1[CH2:31][CH2:30]1)[C:9](N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CC(C)C)=[O:10])(C)(C)C.CN(C)C(=O)CN([C@H](C1C=CC=CC=1)C)C(=O)C[C@@H](CC1N=C(N)SC=1)C(N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CC(C)C)=[O:42].[OH-].[Li+].OO>>[CH:29]1([CH2:28][C@H:8]([CH2:7][C:6]([OH:5])=[O:32])[C:9]([OH:10])=[O:42])[CH2:31][CH2:30]1

Participants

Reactant 3

HCID 6323285(2s)-2-[(2-Amino-1,3-Thiazol-4-Yl)methyl]-N~1~-[(1s,2r,3r)-1-(Cyclohexylmethyl)-2,3-Dihydroxy-5-Methylhexyl]-N~4~-[2-(Dimethylamino)-2-Oxoethyl]-N~4~-[(1s)-1-Phenylethyl]butanediamide

HCID 700739553(R)-(cyclopropylmethyl)-4-{[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxobutanoic acid tert-butyl ester

HCID 86600400Lithium hydroxide hydrogen peroxide

Product 1

HCID 228615522(R)-(cyclopropylmethyl)butanedioic acid

Procedure

The protected amide, 3(R)-(cyclopropylmethyl)-4-{[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxobutanoic acid tert-butyl ester: Following the procedure of section (g) of example 2, the product of section (b) of this example (10.2 g, 30 mmol) was reacted with lithium hydroxide-hydrogen peroxide to give the desired monoprotected dicarboxylic acid, i.e. the 4-tert-butyl ester of 2(R)-(cyclopropylmethyl)butanedioic acid, as a colorless oil (6.65 g, 97%); [α]D23 +16.1° (c 2.61, CHCl3).

Sources & evidence

ORD record: ord-a982e5e50b1447ddb1f7ce20ed3c424e
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541163

Reaction notes

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