Hydrochloric Acid → tert-Butyl [(3S)-1-chloro-4-methyl-2-oxopentan-3-yl]carbamate

HRID 1380613Notes

Reaction equation

HRID 1380613 reaction equation
N(C(OC(C)(C)C)=O)[C@H](C(C=[N+]=[N-])=O)CC1C=CC(O)=CC=1.N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CC1C=CC(O)=CC=1.N(C(OC(C)(C)C)=O)[C@H](C(O)=O)C(C)C.[NH:58]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C@H:59]([C:63]([CH:65]=[N+:66]=[N-:67])=[O:64])[CH:60]([CH3:62])[CH3:61].[ClH:75]>>[NH:58]([C:68]([O:70][C:71]([CH3:73])([CH3:72])[CH3:74])=[O:69])[C@H:59]([C:63]([CH:65]=[N+:66]=[N-:67])=[O:64])[CH:60]([CH3:61])[CH3:62].[NH:58]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C@H:59]([C:63]([CH2:65][Cl:75])=[O:64])[CH:60]([CH3:62])[CH3:61]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 83693Boc-L-ValineHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 54092844HCID 54092844, compoundHCID 131714612HCID 131714612, compound

Product 2

HCID 13919082tert-Butyl [(3S)-1-chloro-4-methyl-2-oxopentan-3-yl]carbamateHCID 54092844HCID 54092844, compound

Procedure

Boc-ValCHN2 was prepared by a procedure substantially similar to that described for preparation of Boc-TyrCHN2 (Procedure C) except that Boc-Tyr-OH was replaced with Boc-Val-OH. Boc-ValCHN2 was treated with 3.45N ethanolic:HCl, as described in Procedure C, to give Boc-ValCH2Cl. After crystallization from hexane, product melted at 70°-73°.

Sources & evidence

ORD record
ord-18e56fe6936441e7a4946c1a88892ae0
Source dataset
uspto-grants-1986_04
Patent number
US04582821

Reaction notes

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