Formaldehyde → HCID 86735458, compound

HRID 616274Notes

Reaction equation

[NH2:1][C@H](C(O)=O)CO.N[C:9]([CH2:15][OH:16])([CH2:13][OH:14])[C:10]([OH:12])=O.C(=O)([O-])[O-].[Na+].[Na+].C=O.ON1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2N=N1>>[C:29]1([C:9]([CH2:13][OH:14])([CH2:15][OH:16])[C:10]([NH2:1])=[O:12])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Reactant 5

HCID 712Formaldehyde

HCID 5951L-Serine

HCID 10340Sodium Carbonate

HCID 757711-Hydroxybenzotriazole

HCID 439893Serine, 2-(hydroxymethyl)-2×

Product 1

HCID 86735458HCID 86735458, compound

Procedure

In Scheme B serine is converted to 2-amino-3-hydroxy-2-hydroxymethylpropionic acid by reaction with aqueous sodium carbonate containing an excess of formaldehyde. From that point the synthesis is conducted as set out in Scheme A. However, it is preferable to activate 2-amino-3-hydroxy-2-hydroxymethylpropionic acid with 1-hydroxy benzotriazole to facilitate condensation with p- N,N-bis(2-chloroethyl)!phenylendediamine. The product, 2-amino-N- p-bis(2-chloroethyl)amino!phenyl-3-hydroxy-2-hydroxymethylpropionamide, is isolated as the hydrochloride salt. As in Scheme A, the hydrochloric acid may be replaced with those indicated acids.

Workup

customcondensation with p- N,N-bis(2-chloroethyl)

Sources & evidence

ORD record: ord-736dbf369e804335b061a7ef3dd9deeb
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04073807

Reaction notes

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