Di-tert-butyl dicarbonate → HCID 13877864, compound

HRID 256085Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][SH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.N[C@H](C(O)=O)CS.C(OC(OC(C)(C)C)=O)(=O)OC(C)(C)C.C(=O)(O)[O-].[Na+].[N+:53]([CH:56]=[CH:57][C:58]1[CH:62]=[CH:61][S:60][CH:59]=1)([O-:55])=[O:54]>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][S:11][CH:57]([C:58]1[CH:62]=[CH:61][S:60][CH:59]=1)[CH2:56][N+:53]([O-:55])=[O:54])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 5

HCID 90495Di-tert-butyl dicarbonate

HCID 152319N-tert-Butyloxycarbonylcysteine

HCID 516892Sodium Bicarbonate2×

HCID 27324183-(2-Nitrovinyl)thiophene

HCID 13293278HCID 13293278, compound

Product 1

HCID 13877864HCID 13877864, compound

Procedure

N-t-butoxycarbonyl-L-cysteine [prepared from 58.6 g of L-cysteine p-toluenesulfonate, 50 g of di-t-butyl pyrocarbonate and 50 g of sodium bicarbonate in the manner described in Example 63(a)] was treated with 32 g of 1-nitro-2-(3-thienyl)ethylene and 6 g of sodium bicarbonate to give 74.8 g of the title compound as a syrup.

Sources & evidence

ORD record: ord-6df92f1fa9f34c37a86a9a6fd5cc3044
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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